3-Amino-2-hydroxybenzoic acid methyl ester Chemical Properties

Melting point:

120℃ (dichloromethane )

Boiling point:

274.9±25.0 °C(Predicted)

Density 

1.305±0.06 g/cm3(Predicted)

storage temp. 

Refrigerator

solubility 

Chloroform, DMSO, Methanol

form 

Solid

pka

9.55±0.10(Predicted)

color 

Light Brown

InChI

InChI=1S/C8H9NO3/c1-12-8(11)5-3-2-4-6(9)7(5)10/h2-4,10H,9H2,1H3

InChIKey

OMWQHVRUXLRZRC-UHFFFAOYSA-N

SMILES

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

Safety Information

Hazard Codes 

Xi

HS Code 

2922500090

3-Amino-2-hydroxybenzoic acid methyl ester Usage And Synthesis

Uses

3-Amino-2-hydroxybenzoic Acid Methyl Ester is disubsituted benzoic acid used in the preparation of various pharmaceutical compounds such as sphingosine kinase inhibitors.

Synthesis

The general procedure for the synthesis of methyl 3-amino-2-hydroxybenzoate from methyl 2-hydroxy-3-nitrobenzoate was as follows: a suspension of methyl 2-hydroxy-3-nitrobenzoate (18.1 g, 93 mmol) with 5% palladium carbon (5 g) in methanol (200 mL) was placed in a Parr flask at room temperature and shaken for 49 hr under hydrogen (60 psi) atmosphere. Upon completion of the reaction, the reaction mixture was filtered through a diatomaceous earth plug and the filtrate was concentrated under reduced pressure to remove the solvent to afford methyl 3-amino-2-hydroxybenzoate (15.6 g, yield > 99%) as a yellow solid. The structure of the product was confirmed by 1H NMR (CDCl3): δ 10.87 (s, 1H), 7.23 (dd, J = 7.7 Hz, 2H), 6.87 (t, J = 9.9 Hz, 1H), 3.95 (s, 3H), 3.80 (br s, 2H); ESI MS m/z 168 [C8H9NO3 + H]+.

References

[1] Patent: WO2004/63155, 2004, A1. Location in patent: Page 172
[2] Patent: JP2016/124812, 2016, A. Location in patent: Paragraph 0138
[3] Patent: US2006/205718, 2006, A1. Location in patent: Page/Page column 73
[4] Patent: EP2959918, 2015, A1. Location in patent: Paragraph 0116
[5] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937

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