O-Phenylenediamine → 2,3-Bis(p-hydroxyphenyl)quinoxaline

HRID 1085643

Reaktionsgleichung

Reaktionsgleichung von HRID 1085643
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:8].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([C:18]([C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=O)=O)=[CH:12][CH:11]=1>C(O)C>[OH:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2[C:18]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[N:8][C:3]3[C:2](=[CH:7][CH:6]=[CH:5][CH:4]=3)[N:1]=2)=[CH:14][CH:15]=1

Komponenten

4

Edukt 2

HCID 7243O-PhenylenediamineHCID 4582044,4'-Dihydroxybenzil

Produkt 1

HCID 4591402,3-Bis(p-hydroxyphenyl)quinoxalineAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Into a 250 ml round bottom flask equipped with a magnetic stirrer and reflux condenser was placed 1,2-diaminobenzene (2.3275 g, 0.0215 mol), 4,4'-dihydroxybenzil (5.2135 g, 0.0215 mol) and absolute ethanol (30 ml). The solution was stirred for one-half hour at room temperature, and a yellow precipitate formed. The mixture was heated to reflux overnight. The solvent was removed by vacuum distillation and the solid dried at 100° C. for two hours to give 6.6 g (97%) of yellow powder. The material was recrystallized from 1,4-dioxane/water mixture. Yield 6.0 g (89%) m.p. 336° C.-338° C. Anal. Calcd for C20H14N2O2 : C, 76.42%; H, 4.49%; N, 8.91%. Found: C, 76.54%; H, 4.44%; N,8.96%.

Aufarbeitung

  1. customInto a 250 ml round bottom flask equipped with a magnetic stirrer
  2. temperaturereflux condenser
  3. customa yellow precipitate formed
  4. temperatureThe mixture was heated
  5. temperatureto reflux overnight
  6. customThe solvent was removed by vacuum distillation
  7. customthe solid dried at 100° C. for two hours

Quellen und Nachweise

ORD-Eintrag
ord-62ac2e4558394bfea352a345c14fb9a5
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05010197

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