Ammonia → 6-Amino-2-fluoronicotinamide

HRID 1059628Notes

Reaction equation

HRID 1059628 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-8cc5c147cf8d4fbdbaf21d64a3c746ef
Source dataset
uspto-grants-2003_02
Patent number
US06521620B1

Reaction notes

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