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

HRID 1281921Notes

Reaction equation

HRID 1281921 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-eb97141a1a1d4da2bf630f4491dd5081
Source dataset
uspto-grants-2002_09
Patent number
US06455534B2

Reaction notes

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