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

HRID 542459Notes

Reaction equation

HRID 542459 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.[OH-].[Na+].O.NN>[Pd].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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 138535735-(4-Nitrophenyl)pyrazin-2(1H)-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

5-(4-Nitrophenyl)-2(1H)-pyrazinone (0.1 g) was warmed with water (2.5 ml) and 1N sodium hydroxide solution (0.46 ml) to about 70° C. To this solution was added 10% Palladium on charcoal (0.01 g), and subsequently hydrazine hydrate (0.1 ml). The well-stirred mixture was heated for 2 minutes, stirred for a further 2 minutes and filtered whilst hot. The filtrate was taken to pH6 with dilute hydrochloric acid, whereupon the solid was collected by filtration, washed with water and dried to give 5-(4-aminophenyl)-2(1H)-pyrazinone (0.07 g).

Workup

  1. temperatureThe well-stirred mixture was heated for 2 minutes
  2. filtrationfiltered whilst hot
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b3e6d0bfa3eb4ffc9b418ef8e88ae029
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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