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

HRID 131321Notes

Reaction equation

HRID 131321 reaction equation
[F: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:22]>C(O)C.Cl>[ClH:22].[F: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 210934602-(4-Fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile

Product 1

HCID 1357977618-Fluoro-2-methyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 73%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4-fluoro-2-nitro-phenylamino)-5-methyl-benzonitrile (1.747 g, 6.44 mmol) in ethanol (35 ml) to 60° C. Add a solution of tin (II) chloride (6.06 g, 31.96 mmol) in 5.0 N hydrochloric acid (35 ml) and heat the resulting mixture to reflux for 40 hours. Cool the reaction to room temperature and place in a freezer for 16 hours. Collect by filtration the product precipitates from the solution to obtain 1.3 g of the title compound (4.68 mmol, 73% yield) as a yellow-green amorphous solid: Mass Spectrum (m/e): 241(M+1).

Workup

  1. temperatureheat the resulting mixture
  2. temperatureto reflux for 40 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationCollect by filtration the product
  6. customprecipitates from the solution

Sources & evidence

ORD record
ord-e5351f042eba4591887fb9796311bda0
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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