2-Amino-4-methylbenzoic acid methyl ester Chemical Properties

Melting point:

35-36℃

Boiling point:

269℃

Density 

1.132

Flash point:

130℃

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

2.42±0.10(Predicted)

Appearance

Light yellow to brown Solid

Safety Information

HS Code 

2916399090

2-Amino-4-methylbenzoic acid methyl ester Usage And Synthesis

Synthesis

1. Concentrated sulfuric acid (1 mL) was added slowly and dropwise to a solution of 2-amino-4-methylbenzoic acid (1.0 g, 6.62 mmol) in anhydrous methanol (10 mL) at 0 °C. 2. The reaction mixture was heated to reflux for 16 hours. 3. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure to remove the solvent. 4. The concentrated crude product was diluted with deionized water (25 mL) and the pH was adjusted to basic with sodium bicarbonate solution (10 mL). 5. The aqueous layer was extracted using ethyl acetate (2 x 50 mL) and the organic phase was collected. 6. The organic phases were combined and washed sequentially with deionized water (50 mL) and saturated saline (50 mL). 7. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford methyl 2-amino-4-methylbenzoate (900 mg, 82% yield) as a yellow liquid.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 3, p. 963 - 968
[2] Tetrahedron, 2009, vol. 65, # 2, p. 563 - 578
[3] Patent: US2011/160231, 2011, A1. Location in patent: Page/Page column 10
[4] Chemische Berichte, 1930, vol. 63, p. 1455,1462
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 10, p. 1919 - 1925

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