Oxalic Acid → 1,4-Dihydrobenzo[g]quinoxaline-2,3-dione

HRID 1781033Notes

Reaction equation

HRID 1781033 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH2:11])[C:2]=1[NH2:12].[C:13](O)(=[O:17])[C:14](O)=[O:15]>Cl>[NH:12]1[C:2]2[CH:1]=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][C:3]=2[NH:11][C:14](=[O:15])[C:13]1=[O:17]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 698722,3-Diaminonaphthalene

Product 1

HCID 108224091,4-Dihydrobenzo[g]quinoxaline-2,3-dioneYield 99.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 603 mg (3.81 mmol) of 2,3-naphthalenediamine and 382 mg (4.24 mmol) of oxalic acid in 5 mL of 2N HCl was refluxed for 3 h and cooled to room temperature. The mixture was filtered, washed with water, and dried to leave a brown solid 803 mg (99%); mp>250° C.; 1H NMR (DMSO-d6), 7.382 (dd, 2, J=3.16, 6.17), 7.525 (s, 2), 7.815 (dd, 2, J=3.22, 6.18), 12.088 (s, 2).

Workup

  1. temperaturewas refluxed for 3 h
  2. filtrationThe mixture was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-63aacc9beb9f47a3a479f15e7d73ef6a
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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