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

HRID 50759Notes

Reaction equation

HRID 50759 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, 87a), 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-b2e4076831f64cffa7be5e23926324a5
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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