Diethyl Oxalate → 2,3-Dihydroxy-6,7-dichloroquinoxaline

HRID 1266133Notes

Reaction equation

HRID 1266133 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.[C:11](OCC)(=[O:17])[C:12](OCC)=[O:13]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[Cl:8])[NH:9][C:12](=[O:13])[C:11](=[O:17])[NH:10]2

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 18452,3-Dihydroxy-6,7-dichloroquinoxaline

Procedure

A mixture of 4,5-dichlorophenylenediamine (54 g, 305 mmol) and diethyl oxalate (124 mL, 146.1 g, 920 mmol) was refluxed overnight, cooled to room temperature, and filtered. The residue was washed with ethanol and dried in vacuo to give the title product as a gray solid powder (67.5 g, 96%); mp>320° C.; IR (KBr, cm−1) 3188, 3156, 3057, 2918, 1724, 1693, 1613, 1497, 1452, 1340, 1338, 1250, 1131, 877, 811, 676, 669, 565; 1H NMR (DMSO) δ 12.00 (s, 2H), 7.18 (s, 2H); 13C NMR (DMSO) δ 154.8, 126.0, 124.4, 116.0; MS (ACPI), m/z 231.0 (M+); Anal. Calcd for C8H4N2O2Cl2: C, 41.59; H, 1.75; N, 12.12. Found: C, 41.60; H, 1.85; N, 12.05.

Workup

  1. temperaturewas refluxed overnight
  2. filtrationfiltered
  3. washThe residue was washed with ethanol
  4. customdried in vacuo

Sources & evidence

ORD record
ord-95dc5a7eae3747f691ce2f2b329abe22
Source dataset
uspto-grants-2003_04
Patent number
US06548499B1

Reaction notes

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