Chemical Properties
brown to black crystalline powder
Uses
3-Amino-2-methylphenol is used in production of (Diimido)dicarboxylic Acid, Imide, Polyamic Acid, Polyamides, Polyesters, and Polyureas.
Synthesis
The general procedure for the synthesis of 2-methyl-3-aminophenol from 2-methyl-3-nitrophenol was as follows: 2-methyl-3-nitrophenol (2.0 g, 13.1 mmol) was dissolved in methanol (50 mL) at room temperature, and 10 wt% palladium carbon catalyst (100 mg) was added. The reaction mixture was stirred under hydrogen atmosphere for 24 hours. Upon completion of the reaction, the palladium carbon catalyst was filtered through diatomaceous earth to remove the palladium carbon catalyst. The filtrate was concentrated under reduced pressure to afford the dark solid product 2-methyl-3-aminophenol (1.62 g, 99% yield). The product was analyzed by 1H NMR (CD3OD, δ=3.31 ppm, 400 MHz) showing: 6.77-6.73 (t, 1H), 6.29-6.27 (d, 1H), 6.22-6.20 (d, 1H), 2.02 (s, 3H). 13C NMR (CD3OD, δ=49.00 ppm, 100 MHz) analysis showed: 156.7,147.5,127.2,110.9,108.8,106.7,9.2. High-resolution mass spectrometry (HRMS-ESI) analysis showed that the calculated value of [M+H]+ (C7H10NO) was 124.0757 and the measured value was 124.0759.
References
[1] Patent: US5952362, 1999, A
[2] Patent: EP887346, 1998, A2
[3] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 87 - 100
[4] Patent: KR2017/31307, 2017, A. Location in patent: Paragraph 0182-0184
[5] Journal of Medicinal Chemistry, 2010, vol. 53, # 5, p. 1964 - 1978
