Author: Jessica.F

Application of 6232-12-8,Some common heterocyclic compound, 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, molecular formula is C10H14ClNO2, 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.

4-Chloro-naphthalimidyl-methylbencoic acid- ethylester (2):; 20.0 g (93.2 mM) 4- aminomethylbencoic acid-ethylester hydrochloride , 21.68 g (93.2 mM) 4-Chloro-l,8-naphthalic anhydride and 19.78 g triethylamine (195.5 mM) in 400 ml DMF were heated to 900C and stirred overnight.[0044] After cooling to room temperature, 100 ml H2O were added to precipitate the desired product.[0045] The 4-Chloro-naphthalimidyl-methylbencoic acid-ethylester was recrystallized from EtOH. Yield: 15.8 g.[0046] The HPLC (Vydac 10-90- 15) shows a single peak at t = 14.04 and the mass peak MH+ = 394.8 ( M = 393.82) was found in the Matrix Assisted Laser Desorption/Ionization Time-of- Flight (MALDI-TOF) mass spectrum.

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

Reference:
Patent; ROCHE DIAGNOSTICS GMBH; F. HOFFMANN-LA ROCHE AG; WO2006/58778; (2006); A2;,
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These common heterocyclic compound, 41191-92-8, name is Ethyl 3-amino-4-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. Safety of Ethyl 3-amino-4-methylbenzoate

EXAMPLE 14 Ethyl 3-[[(5,6-dihydro-2-methyl-1,4-oxathiin-3-yl) carbonyl]amino]-4-methylbenzoate (Compound 14) Thionyl chloride (4.5 g, 0.038 mole) was added to a stirred mixture of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid (6.0 g, 0.037 mole) and methylene chloride (100 ml. The mixture was warmed to 30-35 C. for 3 hours, then evaporated under reduced pressure. The residue, crude 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride, was dissolved in methylene chloride (100 ml), and the ice-chilled solution treated dropwise with a solution of ethyl 3-amino-4-methylbenzoate (6.7 g, 0.037 mole) and triethylamine (4.0 g, 0.040 mole) in methylene chloride (100 ml). The reaction mixture was stirred overnight at room temperature and then worked up by washing in sequence with water, dilute hydrochloric acid, water, 2% sodium hydroxide and water. Evaporation of the solvent gave an oil, which solidified. After recrystallization from ethanol (30 ml), the product (7.1 g, 59% yield) melted at 105-107 C. Analysis: Calc.: C 59.79, H 5.96, N 4.36, Found: C 59.87, H 5.73, N 4.52 NMR: (CDCl3): 1.35 (3H,t), 2.25 (3H,s), 2.3 (3H,s) 2.3 (3H,s), 3.0 (2H,m), 4.15-4.55 (4H,m), 7.1-7.3 (1H,m), 7.55-7.95 (2H,m), 8.45 (1H,d)

The synthetic route of Ethyl 3-amino-4-methylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Uniroyal Chemical Company, Inc.; Uniroyal Chemical Ltd./Ltee; US5268389; (1993); A;,
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Application of 103-09-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 103-09-3 name is 2-Ethylhexyl acetate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Reduce the temperature to 20-25 C, add 39.5kg (0.73kmol) of sodium methoxide solid, start stirring, control the temperature of the kettle at 20-25 C, and add 93.8kg (0.69kmol) of p-methoxybenzaldehyde dropwise within 30min. the temperature was raised to 110 C until the GC content of p-methoxybenzaldehyde was less than 0.25%. It takes about 1h.After the reaction is completed, water is added to the reaction system, stirred, left to stand, and separated into layers.An aqueous layer and an organic layer were obtained. Washing the organic layer to separate the aqueous layer,Obtain a washed organic layer, rectifying the organic layer, the yield of isooctyl p-methoxycinnamate was 183.0 kg (0.63 kmol), and the yield was 91.5%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Ethylhexyl acetate, and friends who are interested can also refer to it.

Reference:
Patent; Anhui Shengnuobei Chemical Technology Co., Ltd.; Liu Qifa; Wang Rong; Yang Jian; Wang Zhongxiao; Li Juan; (12 pag.)CN110540505; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 54810-63-8, name is Methyl 2-chloro-5-methoxybenzoate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 54810-63-8, Recommanded Product: Methyl 2-chloro-5-methoxybenzoate

Methyl (2-chloro-5-methoxy)benzoate (18) (1.19 g, 6.47 mmol) was stirred vigorously in neat aqueous ammonia (28%, 7.8 mL) at room temperature. After 24 h, the resulting mixture was treated with chloroform and the separated organic phase washed with aqueous hydrochloric acid (5 M, 55 mL), water (40 mL), brine (40 mL) then dried (MgSO4), filtered and concentrated under reduced pressure to give 19 as a white powder (0.93 g, 78% yield). m.p. 125.3-126.9 C; IR (ZnSe): 3372, 3178, 1650, 1480, 1461, 1446, 1239, 1028, 821 cm-1; 1H NMR (300 MHz, MeOD): delta 7.34 (1H, d, J = 8.8 Hz), 7.05 (1H, d, J = 2.9 Hz), 7.00 (1H, dd, J = 2.9 and 8.8 Hz), 3.81 (3H, s) ppm; 13C NMR (75 MHz, MeOD): delta 172.1, 159.8, 137.9, 132.0, 122.8, 117.9, 115.2, 56.2 ppm; LRMS (GC-MS): 185 ([M], 60%), 169 ([M-NH2], 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-chloro-5-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Callis, Timothy B.; Reekie, Tristan A.; O’Brien-Brown, James; Wong, Erick C.N.; Werry, Eryn L.; Elias, Nabiha; Jorgensen, William T.; Tsanaktsidis, John; Rendina, Louis M.; Kassiou, Michael; Tetrahedron; vol. 74; 12; (2018); p. 1207 – 1219;,
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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. 85920-63-4, name is 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 5-(1-Hydroxyethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

In an adaptation of general procedure 29b: Acetyl meldrum’s acid (27.4 g, 147 mmol, 3 eq.) and 2-[2-(2-fluoro-6-trifluoromethyl-phenyl)-ethyl]-4,5-dihydro-oxazole-4-carboxyl i c aci d methyl ester (intermediate E.8) (15.6 g, 49.0 mmol) in toluene (300 mL) were heated to reflux for 20 min. Then trifluoro acetic acid (18.9 mL, 27.9 g, 245 mmol, 5 eq.) was added and reflux was continued for 1 hour. The reaction mixture was partitioned between water and ethyl acetate. After phase separation, extraction of the aqueous layer with ethyl acetate, washing of the combined organic layers with brine and evaporation of the solvent flash chromatography yielded the desired title compound (yield: 4.7 g)1H-NMR (methanol-d4, 300 MHz): 3.77 (s, 3H); 3.99 (s, 2H); 4.64 (dd, 1 H); 4.75 (t, 1 H); 5.23 (dd, 1 H); 5.96 (s, 1 H); 7.30 (m, 1 H); 7.38 – 7.47 (m, 1 H); 7.48 – 7.55 (m, 1 H).MS (ESI+): [M + H]+ = 386

According to the analysis of related databases, 85920-63-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; HUeBNER, Jan; WEGSCHEID-GERLACH, Christof; PANKNIN, Olaf; RING, Sven; BAeURLE, Stefan; HUWE, Christoph; NOWAK, Katrin; NUBBEMEYER, Reinhard; MUHN, Hans-Peter; WO2011/76687; (2011); A1;,
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Electric Literature of 260806-90-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 260806-90-4 name is Methyl 3-bromo-2-methoxybenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

To a solution of methyl-3-bromo-2-methoxylbenzoate 6 (1.5 g, 6.12 mmol) in 13 mL of anhydrous 1,4-dioxane were subsequently added bis(pinacolate)diboron (2.3 g, 9.18 mmol), potassium acetate (1.5 g, 15.3 mmol), followed by bis(diphenylphospinoferrocene)palladium dichloride (134.6 mg, 0.184 mmol). The resulting mixture was heated to 110 C in an oil bath for 2 h or to 130 C in a microwave reactor for 30 min (5 bar, 200 W). Afterwards, the solvent was removed under reduced pressure to afford the crude pinacol ester that was used in the following step without further purification. Then, ammonium acetate (1.4 g, 18.36 mmol) and sodium periodate (3.9 g, 18.36 mmol) were added to a solution of the crude pinacol ester in a mixed solution of acetone (11.0 mL) and water (11.0 mL). The resulting mixture was stirred at r.t. until complete conversion of the starting material was observed by TLC. The precipitate was then filtered off, and the filtrate was concentrated under reduce pressure. The residue was extracted with ethyl acetate, and the combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated. The crude product was finally purified by silica gel column chromatography (n-hexane/ethyl acetate 6:4) to give 2-methoxy-3-(methoxycarbonyl)phenylboronic acid 7 (938.6 mg, 4.47 mmol). Yield: 73%. 1H NMR (400 MHz, CDCl3) delta (ppm): 8.04 (dd, 1H, J = 7.4 Hz, J = 1.9 Hz, H4), 7.96 (dd, 1H, J = 7.8 Hz, J = 1.9 Hz, H6), 7.24 (t, 1H, J = 7.5 Hz, H5), 6.15 (bs, 2H, B(OH)2), 3.94 (s, 3H, OCH3), 3.92 (s, 3H, COOCH3).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-bromo-2-methoxybenzoate, and friends who are interested can also refer to it.

Reference:
Article; Bertini, Simone; Chicca, Andrea; Arena, Chiara; Chicca, Stefano; Saccomanni, Giuseppe; Gertsch, Juerg; Manera, Clementina; Macchia, Marco; European Journal of Medicinal Chemistry; vol. 116; (2016); p. 252 – 266;,
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Related Products of 87808-49-9,Some common heterocyclic compound, 87808-49-9, name is Methyl 2-bromo-4-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.

Step 1: Preparation of 3-(2-bromo-4-methylphenyl)pentan-3-ol To a solution of methyl 2-bromo-4-methylbenzoate (10 g, 43.7 mmol) in THF (10 mL) was added dropwise EtMgBr (88 mL, 262 mmol) at 0 C. under nitrogen and then stirred at rt for 12 h. The reaction mixture was quenched with NH4Cl-saturated water and extracted with EA. The combined organic layer was washed with NaHCO3 solution and brine, dried over Na2SO4. The solution was concentrated and the residue was purified by column chromatography over silica gel eluted with PE-EA (10:1?2:1) to provide 3-(2-bromo-4-methylphenyl)pentan-3-ol (8.09 g; yield 71.2%) as a white solid. 1H NMR (400 MHz, CDCl3): delta 7.67 (d, 1H), 7.52 (s, 1H), 7.23 (d, 1H), 2.35 (s, 3H), 1.83 (m, 4H), 0.77 (t, 6H) ppm.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2-bromo-4-methylbenzoate, its application will become more common.

Reference:
Patent; Anacor Pharmaceuticals, Inc.; Eli Lilly and Company; AKAMA, Tsutomu; Balko, Terry William; Defauw, Jean Marie; Plattner, Jacob J.; White, William Hunter; Winkle, Joseph Raymond; Zhang, Yong-Kang; Zhou, Yasheen; US2013/131017; (2013); A1;,
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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. 25081-39-4, name is Methyl 3,5-dimethylbenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 25081-39-4

(iii) Methyl-3,5-bis(bromometylene)benzoate (5) The ester (4, 2.76 g, 0.0168 mol), N-bromosuccinimide (6.07 g, 0.0341 mol) and benzoyl peroxide (85 mg, 0.35 mmol) were placed in 100 ml round-bottom flask. Then dried carbon tetrachloride (25 ml) was added and heated under the reflux conditions for 3 h. After cooling to room temperature, the mixture was filtered and the solvent was evaporated in vacuo to obtain the crude product as residue (5.39 g). The crude product was crystallized from hexane to yield the dibromide (5): 1.37 g (25%), mp. 94-98 C. 1H NMR (300 MHz, CDCl3) delta: 8.00 (s, 2H, arom. H); 7.61 (s, 1H, arom. H); 4.50 (s, 4H, CH2Br); 3.93 ppm (s, 3H, COOCH3).

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

Reference:
Article; Przyby?, Bartosz; Zo?, Jerzy; Janczak, Jan; Journal of Molecular Structure; vol. 1048; (2013); p. 172 – 178;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 31273-66-2, name is Ethyl 2,3-dichlorobenzoate, A new synthetic method of this compound is introduced below., name: Ethyl 2,3-dichlorobenzoate

General procedure: In a fume hood, an oven dried Schlenk flask equipped with a magnetic stirring bar was filled with N2 and evacuated (three cycles). Under N2 atmosphere [Ir(OMe)(COD)]2 (13.3 mg, 0.01 mmol, 1 mol%), 4,4-ditert-butyl-2,2?-bipyridyl (10.7 mg, 0.02 mmol, 2 mol%), and pinacolborane (HBPin) (436 muL, 384 mg, 3 mmol, 1.5 equiv) were added. The appropriate arene substrate (2 mmol, 1 equiv) was added via micropipette under N2 atmosphere. The Schlenk flask was closed and the reaction mixture was heated at 80 C in an oil bath. The progress of reaction was monitored by GC-MS and TLC. Upon completion of reaction, Schlenk flask was cooled to r.t. and exposed to air. The contents of the flask were dissolved in CH2Cl2 (3-5 mL) and taken out in a round-bottomed flask. The volatile organics were removed under reduced pressure using a rotary evaporator. The crude product was purified by column chromatography (silica gel, hexanes-CH2Cl2 1:1).

The synthetic route of 31273-66-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shahzadi, Tayyaba; Saleem, Rahman S. Z.; Chotana, Ghayoor A.; Synthesis; vol. 50; 21; (2018); p. 4336 – 4342;,
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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 6942-39-8 as follows. Recommanded Product: Methyl 2-bromo-5-fluorobenzoate

Example 16a) 2-Bromo-5-dimethylamino-benzoic acid methyl ester (16a)To a stirred solution of 5,24 g (22.5 mmol) 2-Bromo-5-fluoro-benzoic acid methyl ester (Rarechemicals) and 60.0 ml dimethylsulphoxid were added 2.23 g (27.0 mmol) dimethylamine hydrochloride and 6.54 g (47.3 mmol) potassium carbonate. The reaction mixture was stirred for 11 h at 7O0C in an autoclave and was concentrated with high vacuum rotation evaporator at 650C. The residue was diluted with dichloromethane, washed twice with water. The combined water phases were extracted with dichloromethane. The combined dichloromethane phases were washed with diluted sodium hydrogen carbonate solution, dried with sodium sulphate and concentrated. The oily crude was purified by column chromatography and the desired product 16a was obtained in 70 % yield (4,08 g, 15.8 mmol).MS-ESI: 258/560 (M+ +1 , 90/81).Elementary analysis: C 46.53% H 4.69% N 5.43%Determined: C 46,59% H 4.72% N 5.41%

According to the analysis of related databases, 6942-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; WO2008/28688; (2008); A2;,
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