Stannous Chloride → 8-Chloro-2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131338Notes

Reaction equation

HRID 131338 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:10]=2[C:11]#[N:12])=[C:4]([N+:18]([O-])=O)[CH:3]=1.[Sn](Cl)Cl>C(O)C.Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:9]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][C:10]=3[C:11]([NH2:12])=[N:18][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 586258892-(4-Chloro-2-nitro-phenylamino)-5-methyl-benzonitrile

Product 1

HCID 1363885738-Chloro-2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 139.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4-chloro-2-nitro-phenylamino)-5-methyl-benzonitrile (1.63 g, 6.44 mmol) in ethanol (25 ml) to 60° C. To this add a solution of tin (II) chloride (3.22 g, 17.00 mmol) in 5.0 N hydrochloric acid (25 ml). Heat the resulting mixture to reflux for 16 hours. Cool the reaction to room temperature and place in a freezer for 16 hours. Collect by filtration the precipitated product from the solution and to obtain 1.325 g of the title compound (4.50 mmol, 80% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 258(M+1).

Workup

  1. temperatureHeat the resulting mixture
  2. temperatureto reflux for 16 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationCollect by filtration the precipitated product from the solution

Sources & evidence

ORD record
ord-b6a2667b4aa04d2db3d9349a6cdb6b78
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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