5-Cyclopropylpicolinonitrile → (5-Cyclopropylpyridin-2-yl)methanamine

HRID 657735Notes

Reaction equation

HRID 657735 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH2:10]2)=[CH:5][N:4]=1)#[N:2]>N.CO.[Ni]>[CH:9]1([C:6]2[CH:7]=[CH:8][C:3]([CH2:1][NH2:2])=[N:4][CH:5]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 248646065-Cyclopropylpicolinonitrile

Product 1

HCID 55283832(5-Cyclopropylpyridin-2-yl)methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 2-cyano-5-cyclopropylpyridine (210 mg, 1.4 mmol) in 20 mL of 7.0 M ammonia in MeOH was added a small spoon of Raney Ni slurry. The mixture was hydrogenated at 50 psi overnight. The catalyst was filtered off and the filtrate was concentrated to yield a dark oil which was used for the next step reaction without further purification.

Workup

  1. customwas hydrogenated at 50 psi overnight
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated
  4. customto yield a dark oil which
  5. customwas used for the next step reaction without further purification

Sources & evidence

ORD record
ord-48122a820e02416088b6e472e0c4f562
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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