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

HRID 131340Notes

Reaction equation

HRID 131340 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([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])=[C:4]([N+:20]([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]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:10]=3[C:11]([NH2:12])=[N:20][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 24479Stannous ChlorideHCID 586259132-(4-Chloro-2-nitro-phenylamino)-5-isopropyl-benzonitrile

Product 1

HCID 1363841438-Chloro-2-isopropyl-5H-dibenzo[b,e][1,4]diazepin-11-ylamine hydrochlorideYield 198%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Heat a solution of 2-(4-chloro-2-nitro-phenylamino)-5-isopropyl-benzonitrile (0.313 g, 0.99 mmol) in ethanol (6 ml) to 60° C. To this is add a solution of tin (II) chloride (0.752 g, 3.96 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 and place in a freezer for 16 hours. Collect by filtration the precipitated product s from the solution and to obtain 0.316 g of the title compound (0.98 mmol, 99% yield) as a yellow amorphous solid: Mass Spectrum (m/e): 286(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 s from the solution

Sources & evidence

ORD record
ord-982a38d5da114502a2f62dbcc1689042
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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