Stannous Chloride → 7-Fluoro-2-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochloride

HRID 131331Notes

Reaction equation

HRID 131331 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([NH:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:10]=2[C:11]#[N:12])[CH:7]=1.[Sn](Cl)[Cl:24]>C(O)C.Cl>[ClH:24].[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:20]=[C:11]([NH2:12])[C:10]3[CH:13]=[C:14]([CH:17]([CH3:19])[CH3:18])[CH:15]=[CH:16][C:9]=3[NH:8][C:6]=2[CH:7]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 586259572-(5-Fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

Product 1

HCID 692149267-Fluoro-2-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 96%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolvent

Procedure

Heat a solution of 2-(5-fluoro-2-nitro-phenylamino)-5-isopropyl-benzonitrile (0.372 g, 1.24 mmol) in ethanol (6 ml) to 60° C. Add a solution of tin (II) chloride (0.707 g, 3.73 mmol) in 5.0 N hydrochloric acid (6 ml) and heat the resulting mixture to reflux for 16 hours. Cool the reaction to room temperature, add 30 ml of 5.0 N hydrochloric acid and place the mixture in a freezer for 16 hours. Precipitate the product from the solution and collect by filtration. Wash solid with 5.0 N hydrochloric acid to obtain 0.365 g of the title compound (1.19 mmol, 96% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 270(M+1).

Workup

  1. temperatureheat the resulting mixture
  2. temperatureto reflux for 16 hours
  3. temperatureCool
  4. customthe reaction to room temperature
  5. filtrationPrecipitate the product from the solution and collect by filtration
  6. washWash solid with 5.0 N hydrochloric acid

Sources & evidence

ORD record
ord-ba5a2ecf177744bbb8766948fbdb888a
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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