Hydroxyamine hydrochloride → HCID 86742618, compound

Participants

Reaction Steps

A mixture of 5-(4-chlorobenzoyl)-4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid (10.8 g), hydroxylamine hydrochloride (20.7 g) and pyridine (100 ml) was refluxed for 13 hours. After distilling off the solvent, water was added to the mixture which then was rendered acidic with HCl and subjected to extraction with ether. The ether layer was washed with water and dried. By distilling off the solvent, 11.0 g of 5-(4-chloro-α-hydroxyiminobenzyl)4,7-dichloro-2,3-dihydrobenzo[b]furan-2-carboxylic acid was obtained. This compound (11 g) was dissolved in anhydrous dimethylformamide (140 ml), and to the ice-cooled solution, 4.0 g of 60% sodium hydride was added in small portions under agitation. After continuing the agitation for 5 hours at room temperature, the mixture was left to stand overnight. Water was added to the mixture, which then was rendered acidic with HCl and subjected to extraction with ether. The ether layer was washed with water and dried. After distilling off the solvent, the residue was recrystallized from acetone-water, yielding 6.5 g of 5-chloro-3-(4-chlorophenyl)-7,8-dihydrofuro[2,3-g]-1,2-benzisoxazole-7-carboxylic acid. m.p. 240°-243° C. (with decomposition). This compound exhibited a mass spectrum having a molecular ion peak at m/e 349.

Provenance & Evidence