2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 2-Aminobenzo[b]thiophene-3-carboxamide

Participants

Reaction Steps

1.96 grams (10 mmol) of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide was slowly treated with 9.0 grams (40 mmol) DDQ in toluene at room temperature. The reaction was mixed at 40° C. for 15 hours, and monitored by GLC. The solvent was then removed under reduced pressure, and the residue was transferred to 10 ml of dichloromethane and filtered via Celite. The filtrate was purified by chromatography on silica gel, using dichloromethane and ethyl acetate (at an 8:2 ratio), yielding 1.4 grams (70% yield) of 2-aminobenzo[b]thiophene-3-carboxamide as yellow powder.

Provenance & Evidence