Stannous Chloride → 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

HRID 354739Notes

Reaction equation

HRID 354739 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]([N+:19]([O-])=O)[CH:17]=[CH:18][C:13]=2[N:12]([CH3:22])[C:11](=[O:23])[C:10]([CH3:25])([CH3:24])[N:9]=1.[Sn](Cl)Cl>Cl>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH3:22])[C:11](=[O:23])[C:10]([CH3:25])([CH3:24])[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

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 205061565-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one

Product 1

HCID 205061627-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

1.5 g (0.0044 mol) of 5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-7-nitro-2H-1,4-benzodiazepin-2-one are dissolved in 15 ml of concentrated hydrochloric acid, treated with 3.3 g of tin (II) chloride and stirred at room temperature for 15 minutes. The reaction mixture is poured into a mixture of ice and soda solution and extracted with methylene chloride. After drying and evaporating the organic phase, the residue is recrystallised from ether. There is obtained 7-amino-5-(o-fluorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 190°-191°.

Workup

  1. additionThe reaction mixture is poured into a mixture of ice and soda solution
  2. extractionextracted with methylene chloride
  3. customAfter drying
  4. customevaporating the organic phase
  5. customthe residue is recrystallised from ether

Sources & evidence

ORD record
ord-9c4fbeafa6ab4ef5964d0c5a7b80fc0d
Source dataset
uspto-grants-1983_03
Patent number
US04377522

Reaction notes

Loading…