Ammonia → N-[2-(aminomethyl)-4-bromophenyl]pyridine-2-carboxamide

HRID 1786775Notes

Reaction equation

HRID 1786775 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[O:10])=[C:4]([C:17]#[N:18])[CH:3]=1.N.[H][H]>CO.[Ni]>[NH2:18][CH2:17][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[NH:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:10]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 57598297N-(4-bromo-2-cyanophenyl)pyridine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 57598296N-[2-(aminomethyl)-4-bromophenyl]pyridine-2-carboxamideYield 95.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2-2 (3 g, 0.0099 moles) was immediately taken up in a solution of 2.0M ammonia in methanol. To this solution was added catalytic Raney nickel. The reaction was stirred with a hydrogen balloon attached until complete by TLC. Upon completion, the reaction was filtered and the solvent was removed yielding 2.9 grams of 2-3. Analytical LCMS: (CH3CN/H2O/1% TFA, 4 min gradient), 95% pure, M+1 peak m/e 306.

Workup

  1. filtrationUpon completion, the reaction was filtered
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-d09384f53a9941fa81cb1e59be5567db
Source dataset
uspto-grants-2009_03
Patent number
US07507836B2

Reaction notes

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