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

HRID 2287669Notes

Reaction equation

HRID 2287669 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-793b99a443fb4a0497e28cc8b0dd81d2
Source dataset
uspto-grants-2000_07
Patent number
US06084095

Reaction notes

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