Methyl4-amino-2-methylbenzoate Chemical Properties

Boiling point:

302.4±22.0 °C(Predicted)

Density 

1.132±0.06 g/cm3(Predicted)

storage temp. 

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

form 

solid

pka

2.59±0.10(Predicted)

color 

Light brown to brown

InChI

InChI=1S/C9H11NO2/c1-6-5-7(10)3-4-8(6)9(11)12-2/h3-5H,10H2,1-2H3

InChIKey

NRTWXBXJSGGTTE-UHFFFAOYSA-N

SMILES

C(OC)(=O)C1=CC=C(N)C=C1C

Safety Information

HS Code 

2921420090

Methyl4-amino-2-methylbenzoate Usage And Synthesis

Synthesis

Methyl 2-methyl-4-nitrobenzoate (Intermediate 5) (3.25 g, 16.6 mmol) was used as raw material, which was dissolved in ethanol, 10% Pd/C (catalytic amount) and ammonium formate (10.5 g, 0.17 mmol) were added. The reaction mixture was stirred at 40 °C for 2 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the diatomaceous earth was washed with ether. The filtrate and washings were combined and the solvent was evaporated under reduced pressure to give the crude product. The crude product was dissolved in ether and washed with water to remove water-soluble impurities. The organic phase was separated, dried with anhydrous Na2SO4, filtered and evaporated the solvent under reduced pressure to give methyl 2-methyl-4-aminobenzoate as a brown oil (2.8 g, quantitative yield). The structure of the product was confirmed by 1H NMR (300 MHz, CDCl3): δ 7.74 (d, 1H, J = 9.20Hz), 6.41 (m, 2H), 3.75 (s, 3H), 2.47 (s, 3H).

References

[1] Patent: WO2009/47240, 2009, A1. Location in patent: Page/Page column 29
[2] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 942 - 945
[3] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 3, p. 946 - 949
[4] Bulletin de la Societe Scientifique de Bretagne, 1956, vol. 31, p. Sonderheft S.9,41
[5] Patent: WO2006/7542, 2006, A1. Location in patent: Page/Page column 24

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