Ammonia → 6-Amino-2-fluoronicotinamide

HRID 1281974Notes

Reaction equation

HRID 1281974 reaction equation
[F:1][C:2]1[N:10]=[C:9](F)[CH:8]=[CH:7][C:3]=1[C:4]([NH2:6])=[O:5].[NH3:12].O>C(N)=O>[NH2:12][C:9]1[CH:8]=[CH:7][C:3]([C:4]([NH2:6])=[O:5])=[C:2]([F:1])[N:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 105830482,6-Difluoropyridine-3-carboxamide

Product 1

HCID 105348946-Amino-2-fluoronicotinamideYield 31%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

A solution of 2,6-difluoronicotinamide (4.68 g, 0.029 mmol) in dry formamide (30 mL) is saturated with ammonia and allowed to stand at room temperature for 24 h. Water (50 mL) is added and the resultant precipitate is filtered off and washed well with water, to give 6-amino-2-fluoronicotinamide (1.41 g, 31%) mp 236-237° C. 1H NMR (DMSO) δ 7.89 (1H, dd, J=10.4, 8.4 Hz), 7.31, 7.16 (1H, 1H, 2 brs,), 6.93 (2H, brs), 6.36 (1H, dd, J=8.4, 2.4 Hz).

Workup

  1. filtrationthe resultant precipitate is filtered off
  2. washwashed well with water

Sources & evidence

ORD record
ord-f903ef296693427ea73b456abaa6e93a
Source dataset
uspto-grants-2002_09
Patent number
US06455534B2

Reaction notes

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