Hydrochloric Acid → HCID 86737509, compound

Participants

Reaction Steps

9-Hydroximino-4-methylene-9,10-dihydro-4H-benzo[4,5]cyclohepta[1,2-b]thiophene (5.7 g), sodium cyanoborohydride (5.4 g) and methyl orange (0.05 g) are stirred in methanol (150 ml). A solution of concentrated HCl in methanol (1:1 v/v) is added dropwise at a rate sufficient to maintain the mixture at the indicator turning point until thin layer chromatography (silica gel plate, methylene chloride elution) indicates the starting oxime has been consumed (2-3 hours). The mixture is evaporated to dryness in vacuo and the residue is treated with water (250 ml) and adjusted to pH 8 with concentrated ammonia. The mixture is extracted with ether (3×80 ml) and the combined ether layers are washed with water, dried over sodium sulfate, filtered and evaporated to dryness in vacuo to give 9-hydroxamino-4-methylene-9,10-dihydro-4H-benzo[4,5]cyclohepta-[1,2-b]thiophene.

Provenance & Evidence