Methyl 4-amino-3-methoxybenzoate Chemical Properties

Melting point:

128-131°

Boiling point:

332.0±22.0 °C(Predicted)

Density 

1.179±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

form 

solid

pka

2.41±0.10(Predicted)

color 

Red

InChI

InChI=1S/C9H11NO3/c1-12-8-5-6(9(11)13-2)3-4-7(8)10/h3-5H,10H2,1-2H3

InChIKey

DJLFOMMCQBAMAA-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

41608-64-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22

HazardClass 

IRRITANT

HS Code 

2922500090

Methyl 4-amino-3-methoxybenzoate Usage And Synthesis

Uses

Methyl 4-amino-3-methoxybenzoate is mainly used in the preparation of other organic heterocyclic compounds or pharmaceutical small molecule inhibitors.

Synthesis

The general procedure for the synthesis of methyl 4-amino-3-methoxybenzoate from methyl 3-methoxy-4-nitrobenzoate was as follows: methyl 3-methoxybenzoate (83.0 g, 500 mmol) was added drop-wise to a mixture of acids consisting of HNO3 (65% by weight, 40 ml) and H2SO4 (70% by weight, 200 ml) at 0 °C. The reaction mixture was stirred overnight and poured into ice water. The mixture was filtered and the solid filter cake was washed with water (3 x 300 ml) to give 84.4 g of methyl 4-nitro-3-methoxybenzoate as a yellow solid in 80% yield. Next, an ethanol (1500 ml) solution of methyl 4-nitro-3-methoxybenzoate (84.4 g, 400 mmol) was stirred with Pd/C (10% Pd, 5.35 g) catalyst for 5 h under H2 atmosphere. After completion of the reaction, the catalyst was removed by Celite? filtration. The solvent was evaporated in vacuum to give an off-white solid. Finally, the off-white solid was recrystallized from methanol to give methyl 4-amino-3-methoxybenzoate (70.95 g, 392 mmol) in 98% yield.

References

[1] Patent: WO2010/56722, 2010, A1. Location in patent: Page/Page column 360
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 7035 - 7047
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 5, p. 1843 - 1852
[4] Australian Journal of Chemistry, 1988, vol. 41, # 7, p. 1087 - 1097
[5] Patent: CN107698598, 2018, A. Location in patent: Paragraph 0065-0068

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