2-Amino-6-methylbenzoic acid

Chemical Properties

Beige to pink powder

Uses

2-Amino-6-methylbenzoic acid reacts with cyanogen bromide to prepare 2-amino-5-methyl-benzo[d][1,3]oxazin-4-one.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 2-amino-6-methylbenzoic acid from 2-methyl-6-nitrobenzoic acid: Pd/C catalyst (150 mg) was added to a methanol (35 mL) solution of 2-methyl-6-nitrobenzoic acid (1.5 g, 8.29 mmol). The reaction mixture was stirred for 2 hours at room temperature under hydrogen atmosphere. Upon completion of the reaction, the mixture was filtered to remove the catalyst and the filtrate was subsequently concentrated to give 2-amino-6-methylbenzoic acid (1.2 g) in yellow solid form. The product was characterized by liquid chromatography-mass spectrometry (LCMS, ESI mode): the calculated value of C8H9NO2 [M+H]+ was 152 and the measured value was 152, as expected.

References

[1] Patent: US5753664, 1998, A
[2] Tetrahedron Letters, 1984, vol. 25, # 8, p. 839 - 842
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1637 - 1648
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, # 8, p. 1701 - 1714
[5] Journal fuer Praktische Chemie (Leipzig), 1985, vol. 327, # 5, p. 865 - 867