Methyl formate → 5-(Aminomethyl)-2-chloropyridine

HRID 1080366Notes

Reaction equation

HRID 1080366 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.[CH3:10][O:11]C=O>[Co]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH:10]=[O:11])=[CH:4][N:3]=1.[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 7865Methyl formateHCID 51520946-Chloro-3-pyridinecarbonitrile

Product 2

HCID 70209275-(Aminomethyl)-2-chloropyridineHCID 23367277HCID 23367277, compound

Reagents, catalysts & solvents 1

HCID 104730CobaltCatalyst

Procedure

30 g of 91.7% pure 2-chloro-5-cyanopyridine were hydrogenated in 100 ml of methylformate using 7 g of Raney cobalt analogously to Example 2. 2-Chloro-5-(formylaminomethyl)pyridine was obtained in a yield of 92.6% of theory, in addition to 2.9% of theory of 2-chloro-5-(aminomethyl)pyridine.

Sources & evidence

ORD record
ord-72a1f2ee673d4c368a5fe9d0a121c15c
Source dataset
uspto-grants-1996_12
Patent number
US05580983

Reaction notes

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