4-Nitrobenzoyl chloride → 4-Nitro-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

HRID 542452Notes

Reaction equation

HRID 542452 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=2)=[CH:4][CH:3]=1.[N+:15]([C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)([O-:17])=[O:16]>[OH-].[Na+]>[N+:15]([C:18]1[CH:19]=[CH:20][C:21]([C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[N:9]=[CH:10][C:11](=[O:14])[NH:12][CH:13]=3)=[CH:6][CH:7]=2)=[O:23])=[CH:25][CH:26]=1)([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 85024-Nitrobenzoyl chlorideHCID 123580285-(4-Aminophenyl)pyrazin-2(1H)-one

Product 1

HCID 138535664-Nitro-N-[4-(5-oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-(4-aminophenyl)-2(1H)-pyrazinone (1.7 g) in sodium hydroxide was reacted with 4-nitrobenzoyl chloride (1.8 g) in a manner similar to that described in Example 9 to give 5-[4-(4-nitrobenzamido)phenyl]-2(1H)-pyrazinone (1.5 g, m.p. 298°-300° C.).

Sources & evidence

ORD record
ord-f9b05aa3866944c4a6767205aac1407e
Source dataset
uspto-grants-1987_04
Patent number
US04657906

Reaction notes

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