Diethyl Ether → Methyl 3-amino-4-methylthiophene-2-carboxylate

Participants

Reaction Steps

2-Methoxycarbonyl-4-methyl-3-oxotetrahydrothiophene (l.74 g) was dissolved in acetonitrile (13 ml) and the resulting solution was brought to the boil. To this was added hydroxylamine hydrochloride (0.69 g) and the mixture was refluxed for 5 hours. The reaction mixture was cooled in ice and dry ether (50 ml) added whereby a sticky precipitate was produced which was filtered off with the aid of kieselguhr. The kieselguhr was slurried with water and filtered, and the filtrate was basified with ammonia and extracted with ether (2 ×). The combined extracts were dried over sodium sulphate, filtered and evaporated to give the title compound, 1.lg (64%) mp 82°-83°.

Provenance & Evidence