2-Amino-5-methylphenol reacts with bovine hemoglobin to form 2-amino-4,4α-dihydro-4α-7-dimethyl-3H-phenoxazine-3-one, which inhibits the proliferation of Poliovirus in Vero cells. It is converted to dihydrophenoxazinone by purified human hemoglobin.
The general procedure for the synthesis of 6-aminoresorcinol from 6-nitroresorcinol was as follows: 5-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 at low temperature, followed by replacement of air in the system with hydrogen (supplied via a balloon). After the reaction was stirred for 5 h under hydrogen atmosphere, the reaction mixture was filtered through a diatomaceous earth pad and the diatomaceous earth pad was washed with methanol (100 mL). Finally, the combined filtrates were concentrated under reduced pressure to afford 2-amino-5-methylphenol (801 mg, 100% yield).
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