6-Fluoro-3-nitropyridine-2-carboxamide → 3-Amino-6-fluoropyridine-2-carboxamide

HRID 50765Notes

Reaction equation

HRID 50765 reaction equation
[F:1][C:2]1[N:7]=[C:6]([C:8]([NH2:10])=[O:9])[C:5]([N+:11]([O-])=O)=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[NH2:11][C:5]1[C:6]([C:8]([NH2:10])=[O:9])=[N:7][C:2]([F:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 105355166-Fluoro-3-nitropyridine-2-carboxamide

Product 1

HCID 108207923-Amino-6-fluoropyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-fluoro-3-nitropyridine-2-carboxamide (1.50 g, 8.10 mmol) in EtOAc (80 mL) is hydrogenated over 5% Pd-C (0.30 g) at 60 psi for 2 h. After removal of the catalyst by filtration, the solvent is removed under reduced pressure, to give a residue of crude 3-amino-6-fluoropyridine-2-carboxamide which is used directly in the next step. Triethyl orthoformate (60 mL) is added and the mixture is then heated under reflux with vigorous stirring for 18 h. The cooled mixture is diluted with an equal volume of petroleum ether, and the resulting precipitate collected by filtration and is washed well with petroleum ether to give 6-fluoro-3H-pyrido[3,2-d]pyrimid-4-one (1.26 g, 84%). 1H NMR (DMSO) δ 12.72 (1H, brs), 8.31 (1H, dd, J=8.6, 7.7 Hz), 8.20 (1H, s), 7.66 (1H, dd, J=8.6, 3.0 Hz).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-3b3cd5a52661444ea063b751feb2f5eb
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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