Diethyl Ether → Methyl 3-amino-2-thiophenecarboxylate

Participants

Reaction Steps

2-Methoxycarbonyl-3-oxotetrahydrothiophene (2 g) was dissolved in acetonitrile (20 ml) with heating and stirring. Hydroxylamine hydrochloride (0.8 g) was added to the refluxing solution and the mixture was refluxed for 11/2hour. After cooling, ether (50 ml) was added and the precipitated straw-coloured solid was filtered off. The solid was dissolved in water and basified with 4M ammonia solution and extracted with dichloromethane (2×25 ml). The combined extracts were washed with water and with brine and dried over sodium sulphate. Filtration and evaporation gave an oil which solidified on cooling and was crystallised from petrol ether bp 60°-80° to afford the title compound, 1.34 g (73%); mp 62°-63°.

Provenance & Evidence