Diethyl Oxalate → 1,4-Dihydrobenzo[g]quinoxaline-2,3-dione

HRID 984844

Reaktionsgleichung

Reaktionsgleichung von HRID 984844
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[C:13](OCC)(=[O:19])[C:14](OCC)=[O:15]>>[NH:1]1[C:2]2[CH:3]=[C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]3=[CH:10][C:11]=2[NH:12][C:14](=[O:15])[C:13]1=[O:19]

Komponenten

3

Edukt 2

HCID 7268Diethyl OxalateHCID 698722,3-Diaminonaphthalene

Produkt 1

HCID 108224091,4-Dihydrobenzo[g]quinoxaline-2,3-dioneAusbeute 82 %

Versuchsvorschrift

A mixture of 2,3-diaminonaphthalene (2.87 g, 18.14 mmol) and diethyl oxalate (30 mL, 223 mmol) was heated to reflux for 14 hours, cooled to RT and filtered. The residue was washed with EtOH and dried in vacuo to give the title compound as a brown solid (3.15 g, 82%); mp>350° C.; IR (KBr, cm−1) 3045, 2942, 2869,1716, 1642,1406, 877; 1H NMR (DMSO) δ 12.11 (s, 2H), 7.84-7.81 (m, 2H), 7.54 (s, 2H) 7.39 (dd, J=6.3, 3.0, 2H); LC/MS 92.5% (220 nm), m/z (M+H+) 213.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 14 hours
  3. filtrationfiltered
  4. washThe residue was washed with EtOH
  5. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9f035cb72da04937aeb215663ac9e01c
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06869956B2

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