METHYL 2-AMINO-5-METHOXYBENZOATE Chemical Properties

Melting point:

37-38℃

Boiling point:

298.8±20.0 °C(Predicted)

Density 

1.179±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

2.70±0.10(Predicted)

Appearance

Light brown to brown Solid

Water Solubility 

Slightly Soluble (1.1 g/L) (25°C) in water.

Safety Information

HS Code 

2922500090

METHYL 2-AMINO-5-METHOXYBENZOATE Usage And Synthesis

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs.

Synthesis

The general procedure for the synthesis of methyl 2-amino-5-methoxybenzoate from methyl 5-methoxy-2-nitrobenzoate was as follows: methyl 5-methoxy-2-nitrobenzoate (1.60 g, 7.58 mmol) was dissolved in ethyl acetate (14 mL), and 10% palladium-carbon catalyst (containing 50% water, 320 mg) was added. The reaction was stirred at 20-25°C for 3 hours under hydrogen atmosphere (0.25 MPa). Upon completion of the reaction, the palladium-carbon catalyst was removed by filtration and the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography with hexane/ethyl acetate (10:1 to 5:1) as eluent to afford methyl 2-amino-5-methoxybenzoate (1.29 g, 94% yield). The product was characterized by 1H-NMR (CDCl3), δ: 3.76 (3H, s), 3.88 (3H, s), 5.37 (2H, br), 6.63 (1H, d, J = 8.8 Hz), 6.95 (1H, dd, J = 8.8, 3.1 Hz), 7.35 (1H, d, J = 3.1 Hz).

References

[1] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 50
[2] Synlett, 2016, vol. 27, # 8, p. 1237 - 1240
[3] Patent: EP1844768, 2007, A1. Location in patent: Page/Page column 25
[4] Patent: CN106478548, 2017, A. Location in patent: Paragraph 0089; 0090; 0121; 0122; 0137; 0138
[5] Australian Journal of Chemistry, 1972, vol. 25, p. 2621 - 2629

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