Diethyl Ether → 2,3-Bis(3,4-dihydroxyphenyl)quinoxalin-6-ylamine Dihydrochloride

HRID 1272473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1272473
[ClH:1].Cl.[C:3]1([NH2:11])[C:4]([NH2:10])=[CH:5][C:6]([NH2:9])=[CH:7][CH:8]=1.[OH:12][C:13]1[CH:14]=[C:15]([C:20]([C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([OH:31])[CH:25]=2)=O)=O)[CH:16]=[CH:17][C:18]=1[OH:19].C(OCC)C>CO>[ClH:1].[ClH:1].[OH:12][C:13]1[CH:14]=[C:15]([C:20]2[C:22]([C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([OH:31])[CH:25]=3)=[N:10][C:4]3[C:3](=[CH:8][CH:7]=[C:6]([NH2:9])[CH:5]=3)[N:11]=2)[CH:16]=[CH:17][C:18]=1[OH:19]

Komponenten

5

Edukt 3

HCID 3283Diethyl EtherHCID 941791,2,4-Benzenetriamine, hydrochloride (1:2)HCID 2382321,2-Bis(3,4-dihydroxyphenyl)ethane-1,2-dione

Produkt 1

HCID 1356100732,3-Bis(3,4-dihydroxyphenyl)quinoxalin-6-ylamine DihydrochlorideAusbeute 169,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

98.0 mg (0.5 mmol) of 1,2,4-benzenetriamine dihydrochloride and 137.1 mg (0.5 mmol) of 3,3′,4,4′-tetrahydroxybenzil were dissolved in 3 ml of MeOH. The reaction was refluxed for 6 hours. Then the reaction mixture was cooled to r.t. and added dropwise to 40 ml of diethyl ether. The formed dark-red precipitate was collected, washed with ether and dried in vacuo to give 184.0 mg (84.7% yield) of the product. 97.7% purity by LC/MS (230 DAD). Mass-spec [ES+]=362.8. 1H NMR (MeOH-d4) 6.73–6.75 (1H, d), 6.78–6.80 (1H, m), 6.88–6.89 (1H, m), 6.94–6.97 (3H, m), 7.03 (1H, d), 7.49–7.51 (1H, dd), 7.97–7.99 (1H, d).

Aufarbeitung

  1. temperatureThe reaction was refluxed for 6 hours
  2. customThe formed dark-red precipitate was collected
  3. washwashed with ether
  4. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-5539bf14fd874131b83acade6be86104
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208493B2

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