Author: Jessica.F

Some common heterocyclic compound, 762-42-5, name is Dimethyl but-2-ynedioate, molecular formula is C6H6O4, 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. Formula: C6H6O4

General procedure: At room temperature, organic carbonyl acid 3 (R-COOH, 0.5 mmol) was added into a reaction tube equipped with a small magnet. Then a solution of tertiary amine 1 (R1CH2-NR2R3, 0.5 mmol ) in DCM (2.5 mL) was added dropwise in 2 min. After the mixture was stirred at room temperature for a few minutes, 1 equivalents of dimethyl acetylenedicarboxylate (DMAD, 2) was added. The reaction was stirred overnight at room temperature, and then monitored by TLC with silica gel coated plates. After being stirred for 14 h, the solvent was removed and the residue was purified by a flash column chromatography with silica gel with ethyl acetate/hexane (1:25-30) as eluent to give the desired products 4, 5, and 7. Most of compounds are known and confirmed by NMR, ESI-MS, IR.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 762-42-5, its application will become more common.

Reference:
Article; Shen, Hao; Lu, Xing; Jiang, Ke-Zhi; Yang, Ke-Fang; Lu, Yixin; Zheng, Zhan-Jiang; Lai, Guo-Qiao; Xu, Li-Wen; Tetrahedron; vol. 68; 43; (2012); p. 8916 – 8923;,
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Reference of 25081-39-4,Some common heterocyclic compound, 25081-39-4, name is Methyl 3,5-dimethylbenzoate, molecular formula is C10H12O2, 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.

Example 2 Preparation of methyl-3,5-bis(bromomethyl)-benzoate A solution of methyl-3,5-dimethyl-benzoate (16.8 g, 0.10 mol) in carbon tetrachloride (150 ml) was treated with N-bromosuccinimide (35.6 g, 0.20 mmol), and benzoyl peroxide (500 mg, cat. amount), and heated to reflux. After 3 hours, the mixture was cooled to room temperature and filtered through a sintered glass funnel. The filtrate was concentrated under reduced pressure and recrystallized from diethyl ether/hexanes (1:1) to yield the product (18.0 g, 55% yield) as a granular white solid. mp 64-70C. (lit. mp 65-69 C.); TLC (20% ethyl acetate/hexanes): Rf =0.65 (UV active, CAM stain)

The synthetic route of 25081-39-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Trustees of Columbia University in the City of New York; US5342934; (1994); A;,
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Electric Literature of 77820-58-7, 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. 77820-58-7, name is Methyl 2-amino-3-chlorobenzoate, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 97 Preparation of 2-amino-3-chlorobenzyl alcohol A solution of 28.9 g (155 mmol) of methyl 3-chloroanthranilate in 100 ml of ether was added dropwise to a stirred suspension of 7.67 g (202 mmol) of lithium aluminum hydride in 400 ml of ether. After stirring for five hours at room temperature, the grey mixture was treated sequentially with 7.7 ml of water, 7.7 ml of 15% sodium hydroxide and 23 ml of water. The reaction mixture was filtered, and the filtrate was evaporated at reduced pressure. The oily residue was dissolved in ether, and precipitation of the product was induced by addition of hexane. The product was collected by filtration to yield a tan solid in 67% yield, mp 56-68 C. IR and 1 H NMR spectra were in agreement with the assigned structure. Analysis: Calculated for C7 H8 ClNO: C, 53.35; H, 5.12; N, 8.88. Found: C, 53.16; H, 4.84; N, 9.28.

The chemical industry reduces the impact on the environment during synthesis Methyl 2-amino-3-chlorobenzoate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Dow Chemical Company; US4818273; (1989); A;,
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Application of 29006-01-7, The chemical industry reduces the impact on the environment during synthesis 29006-01-7, name is Methyl 4-methoxybutanoate, I believe this compound will play a more active role in future production and life.

8-1. Preparation of Intermediate beta-Diketone Compound 1.8 mol of sodium hydride was added to the solvent ethylene glycol dimethyl ether, and 1 mol of methyl 4-methoxybutanoate was added thereto and stirred at room temperature for 10 minutes. Then, 1.2 mol of t-butylmethylketone was added to the solution which was then stirred at 92 C. for 19 hours. Then, the solution was cooled to room temperature and quenched in 36% hydrochloric acid, after which water and dimethylether were added to and mixed with the solution, and water was removed therefrom. The resulting organic material was washed with 1 wt % sodium hydroxide and then with saturated saline and concentrated, and the residue was fractionated, thereby obtaining the intermediate 8-methoxy-2,2-dimethyloctan-3,5-dione at a yield of 14%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 4-methoxybutanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; CHO, Youn-Joung; WADA, Senji; CHOI, Jung-Sik; LEE, Jin-Seo; SAKURAI, Atsushi; CHO, Kyoo-Chul; YOSHINAKA, Atsuya; SATO, Haruyoshi; UEYAMA., Junji; YOSHINO, Tomoharu; SHIMIZU, Masako; US2012/251724; (2012); A1;,
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Application of 13078-21-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 13078-21-2, name is Ethyl 2-(2-methoxyphenoxy)acetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

rytftro-l-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-l,3- propanediol (2h): (0183) (0184) 2h (0185) Scheme 9. Synthesis of ?’r_yi zro-l-(4-hydroxy-3-methoxyphenyl)-2-(2- methoxyphenoxy)– 1 ,3-propanediol (2h). (0186) This compound was prepared according to the same literature procedure as for compound 2g. Spectral data were consistent with those reported in the literature. JH NMR (400 MHz, CDC13) delta 7.16 (dd, J = 8.2, 1.6 Hz, 1H), 7.04-6.86 (m, 5H), 6.86 (d, J = 8.2 Hz, 1H), 5.71 (b s 1H), 4.96 (d, J = 7.9 Hz, 1H), 4.06-3.97 (m, 1H), 3.90 (s, 3H), 3.87 (s, 3H), 3.73-3.58 (m, 2H), 3.48 (ddd, J = 12.0, 7.8 and 3.6 Hz, 1H), 2.78-2.73 (m, 1H). HRMS (ESI) calculated for CnHzoOeNa [M + Na]+ 343.1158, found 343.1154.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-(2-methoxyphenoxy)acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; WISCONSIN ALUMNI RESEARCH FOUNDATION; STAHL, Shannon, S.; COON, Joshua; RAHIMI, Alireza; ULBRICH, Arne; WO2015/138563; (2015); A1;,
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These common heterocyclic compound, 35472-56-1, name is Ethyl 2-(methylamino)benzoate, 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. Quality Control of Ethyl 2-(methylamino)benzoate

EXAMPLE 26 3-[2-(cis-6-Methoxy-2,3,3a,4,5,9b-hexahydro-[1H]-benz[e]isoindol-1-yl)ethyl]-1-methyl-quinazoline-2,4(1H,3H)-dione hydrochloride N-Methyl-2-carboethoxyaniline (5.0 g, 28 mmol) was treated with 2-chloroethylisocyanate (2.86 mL, 28 mmol) at reflux in toluene for 18 hours. The reaction was cooled to 25 C., and the crystalline product was collected by filtration to yield the intermediate 1-methyl-3-(2-chloroethyl)-quinazoline-2-4-dione.

The synthetic route of Ethyl 2-(methylamino)benzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Abbott Laboratories; US5521181; (1996); A;,
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Synthetic Route of 139911-28-7, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 139911-28-7, name is Ethyl 2-bromo-5-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethyl 2-(2-Methyl-4-fluorophenyl)-5-fluorobenzoate Tetrakis(triphenylphosphine)palladium(O) (0.02 eq, 0.31 g) was added to a vigorously stirred solution of ethyl 2-bromo-5-fluorobenzoate (1.0 eq, 3.3 g, 0.013 mol) and 2-methyl-4-fluorophenylboronic acid (1.2 eq, 0.016 mol, 2.4 g) in 45 mL of toluene, 22 mL of 2M aqueous sodium carbonate, and 11 mL of ethanol and the mixture was refluxed for 9 h. The cooled reaction mixture was poured into 50 mLeach of water, ammonium hydroxide, and 2M aqueous sodium bicarbonate and then filtered through Celite. The filtrate was extracted with ethyl acetate an the organics were dried (MgSO4) and concentrated to yield 3.9 g of a yellow oil. Chromatography (silica gel, 20% ethyl acetate/hexane) gave 3.4 g (92%) of product as a light colored oil. 1 H NMR (CDCl3, 60 mHz) delta7.7 (dd, 1H), 7.5 (m, 1H), 7.25-6.75 (m, 4H), 4.0 (q, 2H), 2.0 (s, 3H), 1.0 (t, 3H); IR (CDCl3 solution) 3130, 2220, 1700, 1450, 1080 cm-1; MS m/z 276 (M+), 201 (base peak).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 2-bromo-5-fluorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Alcon Laboratories, Inc.; US4864028; (1989); A;,
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Application of 66315-23-9,Some common heterocyclic compound, 66315-23-9, name is Ethyl 3-amino-4-(methylamino)benzoate, molecular formula is C10H14N2O2, 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.

Step 2-1-1 Ethyl 1,2-dimethyl-1H-benzimidazole-5-carboxylate Ethyl 3-amino-4-methylaminobenzoate (1.00 g, 5.15 mmol) prepared in the Step 1-1-3 was dissolved in acetic anhydride (4 ml), and the mixture was heated under reflux for 19 hours. After being allowed to cool, the mixture was neutralized with a saturated sodium bicarbonate solution and subjected to extraction with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and then concentrated. The concentrate was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound (1.15 g, quantitative) as a light-brown oily substance. 1H-NMR (CDCl3) delta: 8.39 (d, J=1.5 Hz, 1H), 7.98 (dd, J=1.5, 8.5 Hz, 1H), 7.28 (d, J=8.5 Hz, 1H), 4.39 (q, J=6.9 Hz, 2H), 3.75 (s, 3H), 2.62 (s, 3H), 1.41 (t, J=6.9 Hz, 3H) Mass, m/z: 218 (M+), 173 (base)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 3-amino-4-(methylamino)benzoate, its application will become more common.

Reference:
Patent; Uchida, Hiroshi; Asagarasu, Akira; Matsui, Teruaki; US2013/79306; (2013); A1;,
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Application of 37555-99-0, These common heterocyclic compound, 37555-99-0, name is Diethyl 2-ethoxymalonate, 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.

Part A Preparation of mono-ethyl ethoxymalonate Diethyl ethoxymalonate (10.08 grams, 0.05 mole), prepared as described in Example LXVII, Part B, was saponified with potassium hydroxide (2.77 grams, 0.05 mole) in a mixture of 200 milliliters of ethanol and 0.88 gram (0.05 mole) of water and worked up under conditions similar to those described in Example LIX giving 4.32 grams (0.02 mole) of mono-ethyl ethoxymalonate as a residue product. NMR analysis of the product indicated the following: ‘H NMR(CDCl3) delta1.13-1.49(2xt, 6H, 2*CH3), 3.51-3.95(q, 2H, ether CH2 O), 4.10-4.50(q, 2H, ester CH2 O), 4.53(s, methine CH), 6.95(s, COOH) ppm.

The synthetic route of 37555-99-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rhone-Poulenc Nederland B.V.; US5123951; (1992); A;,
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Application of 871224-19-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 871224-19-0, name is Methyl 3-bromo-2-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of methyl 3-bromo-2-chlorobenzoate (2.3 g, 9.27 mmol) in 1,4-dioxane (20 mL) at room temperature were added (Bpin)2 (3.5 g, 13.91 mmol), KOAc (2.7 g, 27.8 mmol) and Pd2(dppf).CH2Cl2 (0.34 g, 0.46 mmol) and degassed with argon for 5 min. The resulting mixture was maintained at 100 C. for 16 h. The reaction mixture was filtered through celite pad and the filtrate was concentrated under reduced pressure to get methyl 2-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (5 g crude compound) as a dark brown semi-solid. The crude product was used for the next step without purification.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 3-bromo-2-chlorobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Polaris Pharmaceuticals, Inc.; WEBBER, Stephen E.; ALMASSY, Robert J.; (75 pag.)US2018/65917; (2018); A1;,
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