Reaction #2467984

Reaction equation

4-oxo-3-methoxycarbonyltetrahydrothiophene

hydroxylamine hydrochloride

→

title compound

Yield 62.3%

Methyl 4-aminothiophene-3-carboxylate hydrochloride

Yield 62.3%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureunder reflux for 1 h
2. 2
   TemperatureThe mixture was then cooled
3. 3
   Otherthe solid which separated
4. 4
   Filtrationwas filtered off
5. 5
   Washwashed with dry ether

Procedure

A mixture of 4-oxo-3-methoxycarbonyltetrahydrothiophene (6.5 g, 40.62 mmol), hydroxylamine hydrochloride (2.84 g, 40.62 mmol) and acetonitrile (30 mL) was stirred under reflux for 1 h. The mixture was then cooled and the solid which separated was filtered off and washed with dry ether to afford the title compound (4.9 g, 62%), mp 192-196° C.

Source