Category: 4518-10-9

Reference of 4518-10-9, A common heterocyclic compound, 4518-10-9, name is Methyl 3-aminobenzoate, molecular formula is C8H9NO2, 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 solution of B-14a (1 eq.) in toluene is added Ac20 (1.05 eq.) dropwise at reflux and the mixture is stirred at reflux for several minutes. The product B-15a can be crystallized out of the mixture by cooling down and further dilution.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; GOLLNER, Andreas; BROEKER, Joachim; KERRES, Nina; KOFINK, Christiane; RAMHARTER, Juergen; WEINSTABL, Harald; GILLE, Annika; GOEPPER, Stefan; HENRY, Manuel; HUCHLER, Guenther; (365 pag.)WO2017/60431; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 4518-10-9, 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. 4518-10-9, name is Methyl 3-aminobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of methyl 3-aminobenzoate (4.53 g, 30.0 mmol) and triethylamine (3.54 g, 4.88 mL, 35.0 mmol) in dichloromethane (100 mL), at 0 C. while stirring, was added bromoacetyl bromide (6.66 g, 2.9 mL, 33.0 mmol) dropwise. After the addition, the mixture was stirred at room temperature overnight and passed through a short silica pad. The crude product, 3-(2-bromoacetylamino)benzoic acid methyl ester (8.09 g, 99.1%), obtained after the removal of the solvent (>99% by LC/MS, MS (ES+) m/z: 272, 274) was used without further purification.

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

Reference:
Patent; Wilde, Richard G.; Takasugi, James J.; Hwang, Seongwoo; Welch, Ellen M.; Chen, Guangming; US2006/167065; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4518-10-9,Some common heterocyclic compound, 4518-10-9, name is Methyl 3-aminobenzoate, molecular formula is C8H9NO2, 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 13-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18)SCLiOH H2O/TIH F EPO Step 1: (The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (lOlmg, 0.45mmol) and DMAP (8mg, O.Ommol) and stir for lOmin. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2- (2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J Am. Chem. Soc; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1 H, J= 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J= 7.8Hz); 7.78 (t, 1 H, J= 1.8Hz); 7.90 (dd, I H1 J/ = 8.1Hz, J2 = 1.3Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-aminobenzoate, its application will become more common.

Reference:
Patent; REVOTAR BIOPHARMACEUTICALS AG; WO2007/39112; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

The chemical industry reduces the impact on the environment during synthesis 4518-10-9, name is Methyl 3-aminobenzoate, I believe this compound will play a more active role in future production and life. 4518-10-9

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (101mg, 0.45mmol) and DMAP (8mg, 0.06mmol) and stir for 10min. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J. Am. Chem. Soc.; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1H, J = 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J = 7.8Hz); 7.78 (t, 1H, J = 1.8Hz); 7.90 (dd, 1 H, J1 = 8.1Hz, J2 = 1.3Hz).

The chemical industry reduces the impact on the environment during synthesis 4518-10-9. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Revotar Biopharmaceuticals AG; EP1764096; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics