O-Phenylenediamine → 2(1H)-Quinoxalinone, 3-(3,4-dihydroxy-5-nitrophenyl)-

HRID 274460

Reaction equation

HRID 274460 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12](=O)[C:13]([O:15]CCCCCC)=O)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8].[C:23]1([NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH2:29]>CO>[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13](=[O:15])[NH:29][C:24]3[C:23]([N:30]=2)=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 5747978Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, hexyl ester

Product 1

HCID 1356653172(1H)-Quinoxalinone, 3-(3,4-dihydroxy-5-nitrophenyl)-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 396.0 mg of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 137.6 mg of 1,2-phenylenediamine is heated to 120° for 60 minutes. Thereafter, the mixture is suspended in methanol, filtered under suction and recrystallized from N,N-dimethylformamide/water. There is obtained 3-(3,4-dihydroxy-5-nitrophenyl)-2(1H)-quinoxalinone of m.p. >300°.

Workup

  1. temperatureis heated to 120° for 60 minutes
  2. filtrationfiltered under suction
  3. customrecrystallized from N,N-dimethylformamide/water

Sources & evidence

ORD record
ord-c245f17d7eed4973844b162fb366d595
Source dataset
uspto-grants-1995_02
Patent number
US05389653

Linked notes

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