Ammonia → 5-(Aminomethyl)-2-chloroaniline

HRID 1410202Notes

Reaction equation

HRID 1410202 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[C:5]#[N:6].N>CO.[Ni]>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[Cl:10])[CH2:5][NH2:6]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 1044643-Amino-4-chlorobenzonitrile

Product 1

HCID 134650975-(Aminomethyl)-2-chloroaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-Amino-4-chloro-benzonitrile (1.32 g, 8.33 mmol), Ra-Nickel (0.25 g) and 80 ml NH3 in MeOH was stirred for 4 h at rt under H2-atmosphere (3 bar). The mixture was filtered and concentrated and the sub-title compound was used without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customthe sub-title compound was used without further purification

Sources & evidence

ORD record
ord-5a3bb122349746c6a1bc91a430c324ba
Source dataset
uspto-grants-2014_12
Patent number
US08921405B2

Reaction notes

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