2,3-Diaminonaphthalene → Benzo(g)quinoxalin-2(1H)-one, 3-(3,4-dihydroxy-5-nitrophenyl)-

HRID 725326

Reaktionsgleichung

Reaktionsgleichung von HRID 725326
[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].[NH2:23][C:24]1[C:33]([NH2:34])=[CH:32][C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=1>C(O)CCCCC.CO>[OH:1][C:2]1[CH:3]=[C:4]([C:12]2[C:13](=[O:15])[NH:34][C:33]3[CH:32]=[C:31]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]4=[CH:25][C:24]=3[N:23]=2)[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[C:7]=1[OH:8]

Komponenten

5

Edukt 2

HCID 698722,3-DiaminonaphthaleneHCID 5747978Benzeneacetic acid, 3,4-dihydroxy-5-nitro-alpha-oxo-, hexyl ester

Produkt 1

HCID 135624013Benzo(g)quinoxalin-2(1H)-one, 3-(3,4-dihydroxy-5-nitrophenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 81031-HexanolLösungsmittel

Versuchsvorschrift

A solution of 1.07 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 696.3 mg of 2,3-diaminonaphthalene in 3 ml of 1-hexanol is heated to boiling under reflux for 3 hours. The reaction mixture is then cooled and diluted with methanol. The crude product is filtered under suction and recrystallized from N,N-dimethylformamide/water. There is obtained 3-(3,4-dihydroxy-5-nitrophenyl)benzo[g]quinoxalin-2(1H)-one of m.p. >300°.

Aufarbeitung

  1. temperatureunder reflux for 3 hours
  2. temperatureThe reaction mixture is then cooled
  3. filtrationThe crude product is filtered under suction
  4. customrecrystallized from N,N-dimethylformamide/water

Quellen und Nachweise

ORD-Eintrag
ord-a8ac8e0b4ad94140a818b648ff690a0e
Quelldatensatz
uspto-grants-1998_01
Patentnummer
US05705703

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