5-(4-Nitrophenyl)pyrazin-2(1H)-one → 5-(4-Aminophenyl)pyrazin-2(1H)-one

HRID 542456

Reaction equation

HRID 542456 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][C:13](=[O:16])[NH:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 138535735-(4-Nitrophenyl)pyrazin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 123580285-(4-Aminophenyl)pyrazin-2(1H)-oneYield 81.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-(4-Nitrophenyl)-2-(1H)-pyrazinone (0.1 g) was hydrogenated over 10% Palladium on Charcoal (0.01 g) at atmospheric pressure in 50% aqueous dimethylformamide containing 2N sodium hydroxide (0.46 ml). Once the theoretical quantity of hydrogen uptake had been observed, the reaction mixture was filtered and the filtrate treated with HCl to pH6 and evaporated. Trituration of the residue with water afforded the title compound 0.07 g, m.p. 269°-271.5° C. (with decomposition).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionthe filtrate treated with HCl to pH6
  3. customevaporated

Sources & evidence

ORD record
ord-9ea8fa7432e44b85bfda7e7ceeebd41a
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Linked notes

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