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

HRID 984844

Reaction equation

HRID 984844 reaction equation
[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]

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 698722,3-Diaminonaphthalene

Product 1

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

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-9f035cb72da04937aeb215663ac9e01c
Source dataset
uspto-grants-2005_03
Patent number
US06869956B2

Linked notes

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