O-Phenylenediamine → 3-(2-Thienyl)-1,2-dihydroquinoxalin-2-one

HRID 553451

Reaktionsgleichung

Reaktionsgleichung von HRID 553451
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14](=O)[C:15](OCC)=[O:16]>CO>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[C:15](=[O:16])[NH:7][C:2]2[C:1]([N:8]=1)=[CH:6][CH:5]=[CH:4][CH:3]=2

Komponenten

4

Edukt 2

HCID 7243O-PhenylenediamineHCID 77693Ethyl 2-thiopheneglyoxylate

Produkt 1

HCID 7236983-(2-Thienyl)-1,2-dihydroquinoxalin-2-oneAusbeute 70,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of o-phenylenediamine (2.16 g, 20 mmol) and ethyl thiophene-2-glyoxylate (3.68 g, 20 mmol.) in anhydrous methanol (60 mL) was stirred at room temperature for 12 hours under nitrogen atmosphere. The precipitate formed during this time was collected and washed with methanol to give a crude yellow solid, which was recrystallized from ethanol to give pure 3(2-thienyl)quinoxalin-2(1 H)-one (3.2 g, 70%). 1 H NMR (400 MHz, DMSO-d6) δ 12.7 (s, 1 H), 8.39 (d, J=4.4 Hz, 1 H), 7.83 (d, J=5.2 Hz, 1 H), 7.77 (d, J=8.0 Hz, 1H), 7.50 (t, J=7.6 Hz, 1H), 7.35˜7.29 (m, 1 H), 7.22 (t, J=4.8 Hz, 1 H).

Aufarbeitung

  1. customThe precipitate formed during this time
  2. customwas collected
  3. washwashed with methanol
  4. customto give a crude yellow solid, which
  5. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-bf08d39f67eb41638511bdae3c1cb79a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08048862B2

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