METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE Chemical Properties

Melting point:

146-147°

Boiling point:

405.1±35.0 °C(Predicted)

Density 

1.317±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.29±0.10(Predicted)

color 

Light Orange to Light Brown

InChI

InChI=1S/C10H11NO4/c1-6(12)11-7-3-4-8(9(13)5-7)10(14)15-2/h3-5,13H,1-2H3,(H,11,12)

InChIKey

LCXHOHRQXZMSQN-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(NC(C)=O)C=C1O

CAS DataBase Reference

4093-28-1(CAS DataBase Reference)

Safety Information

HazardClass 

IRRITANT

HS Code 

2916399090

METHYL 4-ACETAMIDO-2-HYDROXYBENZOATE Usage And Synthesis

Chemical Properties

Light Brown Solid

Uses

Methyl 4-Acetamido-2-hydroxybenzoate is a reagent used in the synthesis of Mosapride.

Synthesis

Methyl 4-amino-2-hydroxybenzoate (50.7 g, 303.6 mmol) was dissolved in ethyl acetate (750 mL) with stirred water (250 mL) and sodium bicarbonate solution (34.9 g). The mixture was cooled to 0°C over 15 minutes, followed by slow dropwise addition of acetyl chloride (29.7 mL, 415.5 mmol). The reaction mixture was gradually warmed to room temperature and stirred continuously for 2 hours. After completion of the reaction, the organic and aqueous layers were separated, the organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give the white solid product methyl 4-acetamido-2-hydroxybenzoate (63.5 g, 99% yield). The product was confirmed by NMR hydrogen spectrum (CDCl3): δ10.86 (broad single peak, 1H), 7.78 (double peak, J=8.6Hz, 1H), 7.23 (single peak, 1H), 7.16 (broad single peak, 1H), 7.10 (double peak, J=8.6Hz, 1H), 6.13 (broad single peak, 1H), 3.92 (single peak, 3H), 2.19 ( single peak, 3H); mass spectrum (m/z): 208 (MH)+.

References

[1] Patent: WO2013/42135, 2013, A1. Location in patent: Page/Page column 11
[2] Patent: US2014/187581, 2014, A1. Location in patent: Paragraph 0095-0097
[3] Organic Process Research and Development, 2010, vol. 14, # 1, p. 92 - 98
[4] Patent: US2016/251376, 2016, A1. Location in patent: Paragraph 0955; 0956; 0957
[5] Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 22, p. 2657 - 2662

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