6-Chloro-3-nitropicolinamide → 3-Amino-pyridine-2-carboxylic acid amide

HRID 2256095Notes

Reaction equation

HRID 2256095 reaction equation
Cl[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.CO.[Pd]>[NH2:11][C:5]1[C:6]([C:8]([NH2:10])=[O:9])=[N:7][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 105360876-Chloro-3-nitropicolinamide

Product 1

HCID 132387253-Amino-pyridine-2-carboxylic acid amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A solution of 6-chloro-3-nitropicolinamide (2.00 g, 9.91 mmol) in EtOAc/MeOH (1:1, 100 mL) is hydrogenated over 5% Pd-C (0.40 g) at 60 psi for 6 days, with additions of fresh catalyst after 2 and 4 days. After removal of the catalyst by filtration the solution is concentrated to dryness, to give 3-aminopicolinamide as an orange oil, which is used directly in the next step. The crude product is stirred under reflux with triethyl orthoformate (50 mL) for 42 h, during which time a tan precipitate forms. After cooling, the solid is filtered off, washed well with petroleum ether, and dried under vacuum to give 3H-pyrido[3,2-d]pyrimidin-4-one (1.27 g, 87%), mp 343°-345° C. [Price, C. C. and Curtin, D. Y. J. Amer. Chem. Soc. 68, 914, 1946 report mp 346°-347° C⟧

Workup

  1. customafter 2 and 4 days
  2. customAfter removal of the catalyst
  3. filtrationby filtration the solution
  4. concentrationis concentrated to dryness

Sources & evidence

ORD record
ord-4a8a504ae6c9459fb8ec5c94ba79ad7c
Source dataset
uspto-grants-1997_08
Patent number
US05654307

Reaction notes

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