HCID 21529391, compound → 7-Chloro-1-(2,3-dihydroxypropyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 1658441Notes

Reaction equation

HRID 1658441 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH:13]([OH:16])[CH2:14][OH:15])[C:10](=[O:17])[CH2:9][N+:8]([O-])=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:6]=2[CH:26]=1>CO.[Ni]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH:13]([OH:16])[CH2:14][OH:15])[C:10](=[O:17])[CH2:9][N:8]=[C:7]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])[C:6]=2[CH:26]=1

Participants

4

Reactant 1

HCID 21529391HCID 21529391, compound

Product 1

HCID 30504337-Chloro-1-(2,3-dihydroxypropyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

400 mg of 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one 4-oxide are dissolved in 20 ml of methanol, treated with 200 mg of Raney nickel paste and shaken under hydrogen. After uptake of the calculated amount of hydrogen, the mixture is filtered off from catalyst and the clear filtrate concentrated. By chromatography on silica gel with ethyl acetate/methanol (9:1) there is isolated from the residue 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one of melting point 117°-118°C.

Workup

  1. filtrationAfter uptake of the calculated amount of hydrogen, the mixture is filtered off from catalyst
  2. concentrationthe clear filtrate concentrated

Sources & evidence

ORD record
ord-d663073d2a0942fe839fbe38a2434025
Source dataset
uspto-grants-1976_06
Patent number
US03963777

Reaction notes

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