Ammonia → 6-Amino-2-fluoronicotinamide

HRID 2287743Notes

Reaction equation

HRID 2287743 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-6a491429244143a49c2a77101fdfca25
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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