Isophthalonitrile → Benzonitrile, 3-(aminomethyl)-

HRID 1385561Notes

Reaction equation

HRID 1385561 reaction equation
[H][H].[C:3](#[N:12])[C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[CH:5]=1>[Ni]>[C:7]([C:6]1[CH:5]=[C:4]([CH:11]=[CH:10][CH:9]=1)[CH2:3][NH2:12])#[N:8]

Participants

4

Reactant 2

HCID 12276IsophthalonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 457594Benzonitrile, 3-(aminomethyl)-

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

600 g of m-cyanobenzylamine crude product (m-cyanobenzylamine 90% by weight, m-xylylenediamine 10% by weight) obtained by hydrogen reduction of isophthalonitrile in the presence of sponge metal nickel catalyst was added dropwise in 8 kg of water while stirring at room temperature for dissolution and the solution was left to stand overnight at 5C. The crystals which precipitated were filtered by centrifugation to obtain 783 g of m-cyanobenzylamine hydrate (water content: 48% by weight).

Sources & evidence

ORD record
ord-1e9d4fddbbfa4e1d9b63392589dfff14
Source dataset
uspto-grants-2001_07
Patent number
US06262292B1

Reaction notes

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