4-AMINO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

106-107℃

Boiling point:

331.3±37.0 °C(Predicted)

Density 

1.105±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

pka

2.17±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety Information

HS Code 

2922498590

4-AMINO-3,5-DIMETHYL-BENZOIC ACID METHYL ESTER Usage And Synthesis

Synthesis

Scheme 5, Step B. To a solution of methyl 3,5-dimethyl-4-nitrobenzoate (10.0 g, 0.0478 mol) in methanol (100 mL) at 0°C was sequentially added iron powder (15.7 g, 0.2869 mol) and 37% hydrochloric acid (1.72 g, 0.0478 mol). The reaction mixture was heated to 80 °C and kept for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, filtered through a Celite TM bed and the filter cake was washed with methanol. The filtrate was concentrated to dryness to afford methyl 4-amino-3,5-dimethylbenzoate as an unpurified solid (7.8 g, 99% yield). Mass spectrum (m/z): 180.2 (M + 1).

References

[1] Patent: US6342610, 2002, B2. Location in patent: Page column 125
[2] Patent: WO2014/4230, 2014, A1. Location in patent: Sheet 18; 19
[3] Patent: WO2015/94912, 2015, A1. Location in patent: Page/Page column 10
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 1, p. 105 - 109

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