Hydroxyamine hydrochloride → 4-Amino-phenylcarbamoyl-acetohydroxamic acid hydrochloride

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][C:12]([O:14]CC)=O)=[O:10])=[CH:4][CH:3]=1.[ClH:17].[NH2:18][OH:19].[Na]>CO>[ClH:17].[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([CH2:11][C:12]([NH:18][OH:19])=[O:14])=[O:10])=[CH:4][CH:3]=1

Participants

Procedure

A mixture of 17.8 g (0.08 mol) of ethyl 4-aminophenylcarbamoylacetate, 7 g (0.1 mol) of hydroxylamine hydrochloride and 4.6 g (0.2 gram atom) of sodium in 250 ml of anhydrous methanol is left in contact for 2 hours at 20° C. The methanol is evaporated in vacuo, the residue is taken up in 100 ml water and acidified with 6 N HCl and the product is filtered off. Recrystallisation from 80 ml of water gives CRL 40,472. Melting point 164°-165° C. (with decomposition). Yield: 64%.