Acetic Acid → N-(7-Oxo-4,5,6,7-tetrahydro-1-benzothiophen-4-yl)formamide

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Reaction Steps

In 725 ml of 50% aqueous acetic acid, 39 g of N-formyl-4,5,6,7-tetrahydrobenzo[b]thiophen-4-amine is stirred while 473 g of ceric ammonium nitrate is added over 15 minutes at about 25° C. After 15 minutes of additional stirring, sodium chloride is added and the mixture is extracted 3 times with dichloromethane (500, 500 and 250 ml). The combined extract is washed with brine and then with water. The water is extracted with 100 ml of dichloromethane and combined with the main dichloromethane solution. Evaporation of the dichloromethane in vacuo gives a sticky gum, which when triturated with 100 ml of ether affords 28.4 g. of the title compound, m.p. 96° C. to 106° C.

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