2-Amino-3-methylphenol

Chemical Properties

Light yellow solid

Uses

2-Amino-3-methylphenol was used in the preparation of Schiff base ligands.

General Description

2-Amino-3-methylphenol is an aminophenol formed by incubating isopropyl-β-D-thiogalactopyranoside-induced E. coli JS996 strain cells with various nitroaromatic compounds.

Synthesis

The general procedure for the synthesis of 2-amino-3-methylphenol from 2-nitro-3-methylphenol was as follows: 3-methyl-2-nitrophenol (1.0 g, 6.53 mmol) was dissolved in methanol (10 mL) at 23 °C, and Pd/C catalyst (10 wt%, 400 mg) was added. The reaction mixture was deoxygenated under vacuum and then hydrogenated with a hydrogen balloon. After the reaction was carried out under stirring for 5 h, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (100 mL). The combined filtrates were concentrated under vacuum to afford the target product 2-amino-3-methylphenol (803 mg, 100% yield).

References

[1] Patent: US2006/211603, 2006, A1. Location in patent: Page/Page column 68
[2] Patent: EP1346982, 2003, A1
[3] Journal of the Chemical Society, 1925, vol. 127, p. 498
[4] Chemische Berichte, 1961, vol. 94, p. 2551 - 2561
[5] Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3740 - 3744