3-Cyanopyridine → 3-Pyridinemethanamine

HRID 1656111Notes

Reaction equation

HRID 1656111 reaction equation
[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[C:10]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)#[N:11].CN>[Ni]>[CH3:1][NH:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH2:10][NH2:11])[CH:13]=1

Participants

6

Reactant 3

HCID 793-CyanopyridineHCID 6329MethylamineHCID 883933-(Methylaminomethyl)pyridine

Product 2

HCID 310183-PyridinemethanamineHCID 883933-(Methylaminomethyl)pyridine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

For example, in U.S. Pat. No. 2,798,077, "Preparation of Methyl-(beta-picolyl)-Amine," issued to R. Schlapfer et al. in 1957, it is disclosed that 3-cyanopyridine can be hydrogenated in the presence of excess methylamine and a Raney nickel catalyst to yield N-methyl-3-picolylamine and beta-picolylamine. Separation of the beta-picolylamine is then required.

Sources & evidence

ORD record
ord-0b4ccce39f8144a29aaf4f5bec52e81c
Source dataset
uspto-grants-1993_10
Patent number
US05252741

Reaction notes

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