Ammonia → (6-Chloropyridin-2-yl)methanamine

HRID 1838248Notes

Reaction equation

HRID 1838248 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[N:4]=1)#[N:2].N.[H][H]>[Ni].C(O)C>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[N:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 1184246-Chloropyridine-2-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 10313191(6-Chloropyridin-2-yl)methanamineYield 94.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A 3.3 g portion of Raney nickel was suspended in 30 ml of ethanol, and the suspension was mixed with 1.42 g of 2-cyano-6-chloropyridine and 10 ml of 28% aqueous ammonia and stirred at room temperature for 4 hours in a stream of hydrogen. The reaction mixture was filtered through celite and the filtrate was concentrated to obtain 1.38 g of the title compound as a mixture.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-59cfcde9637547569e94d08375fc0b42
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

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