Methyl 4-acetamido-5-chloro-2-methoxybenzoate Chemical Properties

Melting point:

153-156 °C

Boiling point:

440.2±45.0 °C(Predicted)

Density 

1.3248 (rough estimate)

refractive index 

1.6000 (estimate)

storage temp. 

2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

13.16±0.70(Predicted)

color 

White to Off-White

Water Solubility 

1.14g/L at 25℃

InChI

InChI=1S/C11H12ClNO4/c1-6(14)13-9-5-10(16-2)7(4-8(9)12)11(15)17-3/h4-5H,1-3H3,(H,13,14)

InChIKey

OUEXNQRVYGYGIK-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC(Cl)=C(NC(C)=O)C=C1OC

LogP

1.49 at 20℃

CAS DataBase Reference

4093-31-6(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 4-(acetylamino)-5-chloro-2-methoxy-, methyl ester (4093-31-6)

Safety Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

24/25-36-26

WGK Germany 

3

TSCA 

Yes

HS Code 

29242990

MSDS

• Language:English Provider:Methyl 4-acetamido-5-chloro-2-methoxybenzoate
• Language:English Provider:ACROS
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Methyl 4-acetamido-5-chloro-2-methoxybenzoate Usage And Synthesis

Chemical Properties

white to light beige fine crystalline powder

Uses

Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate (Metoclopramide EP Impurity B; Metoclopramide USP Related Compound B) is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent.

Uses

Methyl 4-Acetylamino-5-chloro-2-methoxybenzoate is an biotransformed metabolite of Metoclopramide (M338685), an dopamine D2 receptor antagonist and antiemetic agent.

Synthesis

General procedure for the synthesis of methyl 4-acetamido-5-chloro-2-methoxybenzoate from methyl 4-acetamido-2-methoxybenzoate: 136g of N,N-dimethylformamide (DMF) was added as solvent in a 1L reaction flask, followed by the addition of 50g of methyl 4-acetamido-2-methoxybenzoate, and stirred until it was completely dissolved. To the solution was added 50 g of N-chlorosuccinimide (NCS), which was slowly heated to 40 °C and the reaction was maintained at this temperature for 5 hours. The reaction temperature was then raised to 65 °C and the reaction continued for 4 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and thermo-crystallization was carried out for 8 h. The crude product of methyl 4-acetamido-5-chloro-2-methoxybenzoate was obtained, while the mother liquor of N,N-dimethylformamide was recovered. The crude product was dissolved in 100 g of deionized water, heated to 50 °C and kept for 4 hours, then cooled to 5 °C for filtration. The filtered solid was dried to obtain a white crystalline product, methyl 4-acetamido-5-chloro-2-methoxybenzoate 52.1 g, with a molar yield of 90.3% and HPLC purity ≥99.8%.

References

[1] Patent: CN105523952, 2016, A. Location in patent: Paragraph 0029
[2] Journal of the American Chemical Society, 2006, vol. 128, # 23, p. 7416 - 7417
[3] Archiv der Pharmazie, 1980, vol. 313, # 4, p. 297 - 300
[4] Letters in Drug Design and Discovery, 2012, vol. 9, # 5, p. 489 - 493

Methyl 4-acetamido-5-chloro-2-methoxybenzoate(4093-31-6)Related Product Information

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