Ammonia → 6-Amino-2-fluoronicotinamide

HRID 1386209Notes

Reaction equation

HRID 1386209 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-0b811e2d25ba404590ce699068cd1e21
Source dataset
uspto-grants-2001_07
Patent number
US06265410B1

Reaction notes

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