2-(2-Amino-5-bromophenyl)acetonitrile → 4-Amino-3-cyanomethyl-benzonitrile

HRID 656504Notes

Reaction equation

HRID 656504 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[Cu][C:13]#[N:14]>CN1CCCC1=O.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:13]#[N:14])=[CH:4][C:3]=1[CH2:9][C:10]#[N:11]

Participants

5

Reactant 2

HCID 450370522-(2-Amino-5-bromophenyl)acetonitrileHCID 178418546HCID 178418546, compound

Product 1

HCID 574685124-Amino-3-cyanomethyl-benzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2 mmol of (2-Amino-5-bromo-phenyl)-acetonitrile [882855-95-0] and 4 mmol of copper (I) cyanide are heated at 200° C. in 2 ml of N-methylpyrrolidinone for 4 h. After cooling to room temperature, the solution is diluted with water and extracted with ethyl acetate (3×). The organic layer is separated, dried over magnesium sulphate and evaporated. From the residue the title compound is identified by means of flash chromatography (SiO2 60F) on the basis of the Rf value.

Workup

  1. extractionextracted with ethyl acetate (3×)
  2. customThe organic layer is separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-f3c9c2b3802e4bf897b90a1d94cf78ed
Source dataset
uspto-grants-2011_12
Patent number
US08071774B2

Reaction notes

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