5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one → 7-(1-aminoethyl)-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

HRID 2286166Notes

Reaction equation

HRID 2286166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:14]2[CH:15]=[C:16]([C:19](=[N:21]O)[CH3:20])[CH:17]=[CH:18][C:13]=2[N:12]([CH3:23])[C:11](=[O:24])[CH:10]([CH3:25])[N:9]=1.[H][H]>N.[Ni]>[NH2:21][CH:19]([C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:23])[C:11](=[O:24])[CH:10]([CH3:25])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[F:1])[C:14]=2[CH:15]=1)[CH3:20]

Participants

5

Reactant 2

HCID 736829855-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 205420817-(1-aminoethyl)-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 222AmmoniaSolvent

Procedure

A solution of 4.1 g (12.08 mmol) of 5-(o-fluorophenyl)-1,3-dihydro-7-[1-(hydroxyimino)ethyl]-1,3-dimethyl-2H-1,4-benzodiazepin-2-one in 150 ml of 2 N methanolic ammonia is treated with 5 g of Raney-nickel paste and the suspension is stirred in a hydrogen atmosphere for 24 hours. After filtration of the catalyst and removal of the solvent in vacuo, there is obtained 7-(1-aminoethyl)-5-(o-fluorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one as a foam of melting point 48°-50°.

Workup

  1. filtrationAfter filtration of the catalyst and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-a8d3b9f6a6c84d4089b134a1bf4193b2
Source dataset
uspto-grants-1982_04
Patent number
US04327026

Reaction notes

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