Ammonia → 4-(Aminomethyl)benzonitrile

HRID 736998Notes

Reaction equation

HRID 736998 reaction equation
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.[NH3:11]>CO>[NH2:11][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 826084-(Aminomethyl)benzonitrileYield 16.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Stir 4-bromomethyl-benzonitrile (2.0 g, 0.010 mmoles) in sealed vessel in a solution of 2N ammonia in methanol at 80° C. until completion. Reduce solvent in volume. Dissolve residue in ethyl acetate and wash with 1N HCl. Basify aqueous layer with 5N NaOH. Extract aqueous layer into dichloromethane. Dry organic layer over MgSO4 and reduce in volume to isolate 0.223 g. Yield=16.8%. Mass Spectrum (m/e): (M−).

Workup

  1. washDissolve residue in ethyl acetate and wash with 1N HCl
  2. customto isolate 0.223 g

Sources & evidence

ORD record
ord-67b4c0d10d6d4d25bd89d48fdc1bc7bb
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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