Hydroxyamine hydrochloride → 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one
Reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH3:16])[N:10]=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])[C:8]=2[CH:24]=1)(=O)[CH3:2].Cl.[NH2:26][OH:27]>N1C=CC=CC=1>[F:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:9]1[C:8]2[CH:24]=[C:4]([C:1](=[N:26][OH:27])[CH3:2])[CH:5]=[CH:6][C:7]=2[N:13]([CH3:14])[C:12](=[O:15])[CH:11]([CH3:16])[N:10]=1Participants
4
Procedure
A solution of 4.41 g (13.60 mmol) of 7-acetyl-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one and 4.41 g (63.46 mmol) of hydroxylamine hydrochloride in 250 ml of pyridine is stirred at room temperature for 19 hours, subsequently poured on to ice and extracted with chloroform. The organic extracts are washed successively with 2 N hydrochloric acid and water, dried and evaporated. After chromatography of the residue on 250 g of silica gel using chloroform/ethanol (98:2) as the elution agent, there is obtained 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one of melting point 101°-103°.