Month: September 2021

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 18595-14-7, name is Methyl 4-amino-3-methylbenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 18595-14-7

Into a 500-mL round-bottom flask was placed a solution of methyl 4-amino-3-methylbenzoate (4.00 g, 24.2 mmol, 1.00 equiv) and NaSCN (7.00 g, 86.4 mol, 3.57 equiv) in AcOH (90 mL) that was cooled to 0 C. This was followed by the addition of a solution of Br2 (3.9 g, 25 mmol, 1.0 equiv) in AcOH (25 mL) dropwise, maintaining at 0 C over 20 min. The resulting solution was allowed to warm to RT on its own accord (over approximately 10 min.) and stirred for 48 hrs at RT. At this time, the solids of the reaction were filtered out. The resulting solution was diluted with 100 mL H20. The pH value of the solution was adjusted to 8-9 with ammonia (using Whatman PH strip paper to monitor PH adjustment) which furnished an immediate precipitation. The solids were collected by filtration and washed once with ice cold MeOH (50 mL) to afford as a yellow solid. MS m/z 223.0 (M+l). 1H NMR (400 MHz, MeOH- 4) delta 8.17 (app d, J = 1.0 Hz, 1H), 8.03 (br s, 2H, NH2), 7.68 (s, 1H), 3.82 (s, 3H), 2.42 (s, 3H).

According to the analysis of related databases, 18595-14-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; IRM LLC; TULLY, David C.; RUCKER, Paul Vincent; ALPER, Phillip B.; MUTNICK, Daniel; CHIANELLI, Donatella; WO2012/87519; (2012); A1;,
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In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 35418-07-6 as follows. Computed Properties of C10H13NO2

General procedure: To a solution of 3a (1 g) in ethanol was added Pd/C (5%, 0.1 g) and the mixture was stirred for 24 hrs at room temperature in a hydrogen atmosphere under atmospheric pressure. Insoluble matters were removed using Celite, and the filtrate was concentrated in vacuo to give the desired product 4a (0.76 g) as a yellow solid. To a solution of carboxylic acid (1 equiv) in CH2Cl2 (15 mL) at 0 C was added DMAP (1 equiv) and EDCI (1 equiv). The reaction mixture was stirred at 0 C for 45 minutes. At this time 4a (1 equiv) was added and the mixture was warmed to room temperature and stirred overnight. The resulting mixture was concentrated in vacuo, partitioned between 1.0 M HCl (20 ml) and ethyl acetate (3×20 mL). The combined organic layers were washed with brine (2 × 15 ml), dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatograph using a mixture of petroleum ether/ethyl acetate (20 : 5, v/v) as eluent to afford the product as a white solid. To a solution of the obtained solid (1 equiv) in 2:3:1 THF/MeOH/H2O (18 ml) was added LiOH·H2O (1.5 equiv). After stirring at room temperature for 4 h, the volatiles were removed under reduced pressure. The residue was acidified with 1N hydrochloric acid solution, and then filtered and the filter cake was washed with 5 mL of water, dried in vacuum to afford a white powder. Recrystallization from 75% EtOH gave the desired compounds 2-17 as white solid.

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yang, Jianyong; Li, Zheng; Li, Huilan; Liu, Chunxia; Wang, Nasi; Shi, Wei; Liao, Chen; Cai, Xingguang; Huang, Wenlong; Qian, Hai; Bioorganic and Medicinal Chemistry; vol. 25; 8; (2017); p. 2445 – 2450;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5048-82-8, name is Ethyl 3-(4-aminophenyl)acrylate, This compound has unique chemical properties. The synthetic route is as follows., Formula: C11H13NO2

The appropriate amino acid derivative from Example 9 (0.020 g, 0.05 mmol) was dissolved in DCM (1 mL). DMAP (0.018 g, 3 equivalents), Et3N (20 muL, 0.15 mmol, 3 equivalents), BroP (0.058 g, 0.15 mmol, 3 equivalent), and ethyl-4-aminocinnamate (0.029 g, 0.015 mmol, 3 equivalents) were added and the mixture stirred for 20 h at room temperature. Camphor-10-sulfonic acid (CSA; 0.046 g, 0.2 mmol, 4 equivalents) was added and the reaction mixture was stirred for an additional 24 h at room temperature.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5048-82-8.

Reference:
Patent; Boehringer Ingelheim (Canada) Ltd.; US2003/236251; (2003); A1;,
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These common heterocyclic compound, 122-72-5, name is 3-Phenylpropyl Acetate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C11H14O2

General procedure: A general procedure for the manganese-catalysed benzylic amination is as follows. A Teflon stir bar and 5 A powdered molecular sieves (40 mg) were added in a 10 ml round-bottom flask, which was sealed with a Suba Seal rubber septum, placed under vacuum, flame-dried for 45 s to activate the molecular sieves, cooled under a purged and completely air-free argon balloon and wrapped in foil to exclude light. Once cooled, solvent (0.40 ml, 0.5 M to substrate) and substrate (0.20 mmol, 1 equiv.) were added and stirred for 10 min. Manganese(iii) perchlorophthalocyaninechloride 3 (23.1 mg, 0.020 mmol, 0.1 equiv.) and silver hexafluoroantimonate (6.9 mg, 0.020 mmol, 0.1 equiv.) were weighed in a foil-wrapped 1-dram vial in the glove box and sealed with a Teflon cap. The vial was removed from the glove box and the contents added directly to the round-bottom flask while maintaining an argon atmosphere, then stirred for 10 min at room temperature. In a 1-dram vial open to air, 2,2,2-trichloroethyl (phenyl-lambda 3-iodanylidene)sulfamate (172.2 mg,0.40 mmol, 2 equiv.) was weighed and added directly to the round-bottom flask while maintaining an argon atmosphere. The Suba Seal rubber septum was replaced by a polyethylene cap, sealed tightly, and placed in a 40 C oil bath for 8 h with stirring. Upon reaction completion, the reaction was filtered through a 1 inch silicagel plug using diethyl ether or ethyl acetate as the eluent. The crude material was concentrated and dry-loaded directly onto a silica gel column.

The synthetic route of 3-Phenylpropyl Acetate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Clark, Joseph R.; Feng, Kaibo; Sookezian, Anasheh; White, M. Christina; Nature Chemistry; vol. 10; 6; (2018); p. 583 – 591;,
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These common heterocyclic compound, 175278-29-2, name is Methyl 5-fluoro-2-methylbenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Computed Properties of C9H9FO2

A mixture of methyl 5-fluoro-2-methylbenzoate (0.5 g, 3.0 mmol),NBS (0.18 g, 3.0 mmol), and di-benzoyl peroxide (BPO) (36 mg, 0.15 mmol) in 1,2-dichloroethane (5 mL) was heated at 80 C for 12 huntil all starting material was consumed. The reaction was cooled to room temperature, and the precipitated solid was removed by filtration and washed with ethers (10 mL). The filtrate was concentrated in vacuo and the residue was partitioned between 2 N NaHCO3 (15 mL) and ethers (15 mL). The organic layer was separated, dried over MgSO4, filtered and concentrated to give a crude product (0.65 g, 89%), which was used in the next step reaction without further purification.

The synthetic route of Methyl 5-fluoro-2-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Huang, Junli; Deng, Xiaoyan; Zhou, Siru; Wang, Na; Qin, Yujun; Meng, Liuwei; Li, Guobao; Xiong, Yuhua; Fan, Yating; Guo, Ling; Lan, Danni; Xing, Junhao; Jiang, Weizhe; Li, Qing; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 644 – 654;,
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Electric Literature of 455-75-4, A common heterocyclic compound, 455-75-4, name is Ethyl 3-amino-4-fluorobenzoate, molecular formula is C9H10FNO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

Intermediate 33: N-{5-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide; Step A: Ethyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-4-fluorobenzoate; To a solution of ethyl 3-amino-4-fluorobenzoate (5.47 g, 30 mmol) and pyridine (2.55 mL, 33 mmol) in DCM (150 mL) was added 2,6-difluorobenzenesulfonyl chloride (4.45 mL, 33 mmol). The reaction was stirred overnight at rt. After 16 h, the reaction mixture was concentrated, triturated with ether, and dried in vacuo to generate 7.87 g (66% yield) of the product of Step A as a white powder. MS (ESI): 360 (M+H).

The synthetic route of 455-75-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Adams, Jerry Leroy; Dickerson, Scott Howard; Johnson, Neil W.; Kuntz, Kevin; Petrov, Kimberly; Ralph, Jeffrey M.; Rheault, Tara Renae; Schaaf, Gregory; Stellwagen, John; Tian, Xinrong; Uehling, David Edward; Waterson, Alex Gregory; Wilson, Brian; US2009/298815; (2009); A1;,
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Reference of 148547-19-7,Some common heterocyclic compound, 148547-19-7, name is Methyl 4-bromo-3-methylbenzoate, molecular formula is C9H9BrO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of methyl-4-bromo-3-methylbenzoate (5.7 g, 24. 88-MMOL), lithium aluminum hydride (29 mL, 29 mmol, 1 M solution in tetrahydrofuran) and tetrahydrofuran (100 mL) is stirred in ice/water for 1 hr. The reaction is quenched with aqueous hydrochloric acid (50 mL, 1 M). The product is extracted into ethyl acetate (3 * 100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The crude product is taken up in propionitrile (100 mL). Methyl acrylate (10 mL, 121.5 mmol), palladium acetate (1.12 g, 5 mmol), tri-o-tolylphosphine (3.0 g, 10 mmol), and N, N-diisopropyl ethylamine (8.7 mL, 50 mmol) are sequentially added and the resulting reaction mixture is heated to 110 C 3 hr. The mixture is concentrated, and the residue diluted with aqueous hydrochloric acid (100 ML, 1M). The product is extracted with dichloromethane (2 * 100 mL) and ethyl acetate (100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered, concentrated, and purified via silica chromatography eluting with 7: 3 hexanes: ethyl acetate to 1 : 1 hexanes: ethyl acetate to afford the pure product as a yellow oil, 4.7 g, 91 %. MS M+1 207. The structure is confirmed by : L H NMR spectroscopy.

The synthetic route of 148547-19-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2004/63184; (2004); A1;,
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Some common heterocyclic compound, 2150-38-1, name is Methyl 3,4-dimethoxybenzoate, molecular formula is C10H12O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. COA of Formula: C10H12O4

Example 1 Synthesis of 3,4-dimethoxy(4,4-dimethyl-3-oxopentanoyl)benzene In a 200 ml three-necked flask equipped with a mechanical stirrer, dropping funnel, reflux condenser, and a nitogen-inlet tube, 2.45 gm (61 mmol) of 60% sodium hydride, 10 gm (51 mmol) of methyl 3,4-dimethoxybenzoate, and 100 ml of anhydrous tetrahydrofuran were mixed with stirring under nitrogen stream, and refluxed with heating while 6.1 gm (61 mmol) of pinacolone was added dropwise. The refluxing under heat was continued for 7 hours. After cooling the reaction mixture, 30 ml of 2N hydrochloric acid was added and the mixture was extracted twice with chloroform. The extract was dried over anhydrous sodium sulfate and the solvent was removed by evaporation to give a crude product. Hexane was added to the crude product and insoluble substances were filtered off. The filtrate was concentrated by evaporation, and recrystallization afforded 8.9 gm of the target compound as colorless needles (yield: 65%). Melting Point: 52.3-53.3 C. IR(gammaKBr, cm-1): 1602, 1521, 1470, 1446, 1365, 1299, 1266, 1218, 1188, 1131, 885, 786, 729. 1 H-NMR(CDCl3, delta): 1.26(9 H, s, t-C4 H9), 3.95(3 H, s, OCH3), 3.96(3 H, s, OCH3), 6.24(1 H, s), 6.90(1 H, d, J=8.4 Hz), 7.49(1 H, s), 7.51(1 H, d, J=8.4 Hz). Elemental analysis: Calculated (%) C: 68.16, H: 7.63; Found (%) C: 68.23, H: 7.60.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2150-38-1, its application will become more common.

Reference:
Patent; Kao Corporation; US5146002; (1992); A;,
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Reference of 394-35-4, A common heterocyclic compound, 394-35-4, name is Methyl 2-fluorobenzoate, molecular formula is C8H7FO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a reactor under nitrogen atmosphere was added a toluene solution of ester 6 (LOO Wt, 1.0 eq), methyl 2-fluorobenzoate (0.91 Wt, 0.75 Vol 1.10 eq)5 and THF (0.53 Wt, 1.8 Vol). The solution was cooled to below -70 C. Lithium hexamethyldisilazide (LiHMDS, 1.0M in THF, 7.6 Wt, 8.6 Vol, 1,6 eq) was added at such rate that the internal temperature does not exceed -60°C.. After completion of the LiHMDS addition, the mixture was warmed (rate between 10-20C/h) and stirred at -40C for 1h. The reaction was monitored by GC (Conversion Target >95percent). If after 4h the conversion is still under targeted amount, additional LiHMDS 1M in THF was added (1.1 eq based on unreacted starting material). After achieving the target conversion, the internal temperature was raised (rate between 20-30°C/h) to 15 to 20 °C. 25 wtpercent aqueous ammonium chloride (1,7 Wt, 1.6 Vol) was added to the reactor keeping the internal temperature below 0 °C Upon completion of the addition, the mixture was warmed to ?0°C, and transferred to a vessel containing 25 wtpercent aqueous ammonium chloride (4.4 Wt, 4.1 Vol) and water (1.1 Wt, 1.1 Vol).The mixture was stirred for at least 30 min at 20-25 °C. The lower aqueous layer was removedand the organic layer was washed with 20 wt percent aqueous sodium chloride (3.0 Wt, 1.4 Vol). The mixture was stirred for at least 15 minutes then allowed to settle. The lower aqueous layer was removed. The organic phase was concentrated under reduce pressure (Jacket < 25 °C) untildistillation ceases. Toluene (6.6 Wt, 6.7 Vol) was added and the resulting mixture was washedwith water (3.0 Wt, 3.0 Vol), stirred for at least 15 min, then allowed to settle. The organics werewashed with water (3.0 Wt, 3.0 Vol) until pH is constant at pH=78. The organic phase was washed with 20percent aqueous sodium chloride (3.0 Wt, 1.4 Vol). The organic phase was concentrated under reduced pressure (jacket <25°C) to afford ketoester 11 (2.1 Wt) as an orangeoil. The synthetic route of 394-35-4 has been constantly updated, and we look forward to future research findings. Reference:
Patent; ???????????????????????????; ? Buranko; Kimu ?; Chan ?; ?; Yoshizawa Kazuhiro; (94 pag.)JP2016/121177; (2016); A;,
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Related Products of 54535-22-7, A common heterocyclic compound, 54535-22-7, name is Diethyl 2-((phenylamino)methylene)malonate, molecular formula is C14H17NO4, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

j00330J A 1 L three-necked flask fitted with a mechanical stirrer was charged with 2- phenylaminomethylene-malonic acid diethyl ester (26.3 g, 0.100 mol), polyphosphoric acid (270 g) and phosphoryl chloride (750 g). The mixture was heated to 70 C and stirred for 4 h. The mixture was cooled to room temperature and filtered. The residue was treated with aqueous Na2CO3 solution, filtered, washed with water and dried. 4- Hydroxyquinoline-3-carboxylic acid ethyl ester was obtained as a pale brown solid (15.2 g, 70%). The crude product was used in next step without further purification.

The synthetic route of 54535-22-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; CHU, Cathy; DOKOU, Eleni; HASELTINE, Eric L.; MOSKOWITZ, Samuel; OVERHOFF, Kirk A.; ROBERTSON, Sarah; WALTZ, David; (204 pag.)WO2019/10092; (2019); A1;,
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