Ammonia → 6-Amino-2-fluoronicotinamide

HRID 2256174Notes

Reaction equation

HRID 2256174 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-ea483090fd004c038894c25409b88815
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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