Oxalic Acid → 5-Nitro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

HRID 53818Notes

Reaction equation

HRID 53818 reaction equation
[N+:1]([C:4]1[C:5]([NH2:15])=[C:6]([NH2:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].[C:16](O)(=[O:20])[C:17](O)=[O:18]>Cl>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[C:6]2[C:5]=1[NH:15][C:16](=[O:20])[C:17](=[O:18])[NH:14]2)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 50660631,2-Benzenediamine, 3-nitro-5-(trifluoromethyl)-

Product 1

HCID 211899645-Nitro-7-trifluoromethyl-1,4-dihydro-2,3-quinoxalinedione

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 3-nitro-5-trifluoromethyl-1,2-phenylenediamine (0.560 g, 2.53 mmol) and oxalic acid (0.325 g, 2.58 mmol) in 2N HCl (8.5 mL) was refluxed for 6 h. The suspension was then cooled to r.t. and the solid filtered, washed with water (5.0 mL) and dried under vacuum to yield 0.502 (72%) of pure title compound as a yellow brown powder, m.p. 329°-332° C.; 1H NMR (DMSO-d6): 7.640 (s, 1H), 8.111 (s, 1H), 11.414 (s, 1H), 12.432 (1H).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationthe solid filtered
  3. washwashed with water (5.0 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a7658428cef645fd9e9889de91ca2900
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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