Sodium Hydroxide → rac-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

HRID 2199039Notes

Reaction equation

HRID 2199039 reaction equation
[Cl: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]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[N:12]([CH3:22])[C:11](=[O:23])[CH:10]([CH3:24])[N:9]=1.[OH-].[Na+]>Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:22])[C:11](=[O:23])[CH:10]([CH3:24])[N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20443626(+)-5-(o-chlorophenyl)--1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 10335749rac-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

108.9 g (0.316 mol) of rac-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 750 ml of concentrated hydrochloric acid. 215 g (0.95 mol) of stannous chloride are added portionwise to the solution while cooling with ice and stirring and the mixture is stirred at room temperature for 3 hours. The mixture is subsequently neutralised at 0° C. with 10 N sodium hydroxide and the aqueous phase is extracted with methylene chloride/ethanol (4:1). The organic phase is washed with water, dried and evaporated. Recrystallisation of the residue from ethyl acetate/petroleum ether yields rac-7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3-dimethyl-2H-1,4-benzodiazepin-2-one of melting point 180° C.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture is stirred at room temperature for 3 hours
  3. extractionthe aqueous phase is extracted with methylene chloride/ethanol (4:1)
  4. washThe organic phase is washed with water
  5. customdried
  6. customevaporated
  7. customRecrystallisation of the residue from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-ad47e84d01734aad9725437775eca4f9
Source dataset
uspto-grants-1982_11
Patent number
US04361511

Reaction notes

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