Ammonia → 5-Chloro-3-pyridineethanamine

HRID 1749468Notes

Reaction equation

HRID 1749468 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH2:8][N+]#[C-])[CH:7]=1.[NH3:11].[CH3:12]O>[Ni]>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:12][NH2:11])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 131733584HCID 131733584, compound

Product 1

HCID 538801475-Chloro-3-pyridineethanamine

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a solution of 3-chloro-5-(isocyanomethyl)pyridine (810 mg, 5.36 mmol) in MeOH (15 mL) was added Raney-nickel and ammonia. The resulting reaction mixture was stirred at room temperature for 5 h under hydrogen. The reaction mixture was filtered and the filtrate was concentrated to afford the crude title compound (780 mg, crude). MS (ESI) m/z 157.0 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-99cc38e810e148698d7b338ee173c1c6
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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