6-Chloro-3-nitropicolinamide → 3-Amino-6-chloropyridine-2-carboxamide

HRID 50769Notes

Reaction equation

HRID 50769 reaction equation
[Cl: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]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 1

HCID 105360876-Chloro-3-nitropicolinamide

Product 1

HCID 107497043-Amino-6-chloropyridine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 6-chloro-3-nitropicolinamide (0.30 g, 1.49 mmol) in EtOAc (30 mL) is hydrogenated at 60 psi over 5% Pd-C (0.10 g) for 20 min. After removal of the catalyst by filtration the solution is concentrated to dryness to give 3-amino-6-chloropicolinamide as a yellow oil, which is used directly in the next step. It is dissolved in triethylorthoformate (30 mL) and the mixture is heated under reflux for 18 h. Petroleum ether (30 mL) is added to the cooled solution, and the resulting precipitate of crude 6-chloro-3H-pyrido[3,2-d]pyrimidin-4-one (0.27 g, 99%) is filtered off and dried in a vacuum oven.

Workup

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

Sources & evidence

ORD record
ord-0b55e897e8624bf6a1d9dae1c43d84f3
Source dataset
uspto-grants-2004_03
Patent number
US06713484B2

Reaction notes

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