Oxalic acid dihydrate → HCID 19827847, compound

HRID 1494324Notes

Reaction equation

HRID 1494324 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[C:21](O)(=[O:25])[C:22](O)=[O:23]>Cl>[CH2:1]([N:8]1[C:9]2[C:10](=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[NH:18][C:22](=[O:23])[C:21]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 4381698N~1~-Benzyl-4-nitrobenzene-1,2-diamine

Product 1

HCID 19827847HCID 19827847, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0.5 g (2.1 mmol) N-benzyl-2-amino-4-nitroaniline and 0.55 g (4.4 mmol) oxalic acid dihydrate in 30 ml 4N hydrochloric acid was refluxed for 5 h. After cooling to 25° C. the product was filtered off and washed with water. The crude product was recrystallized (dimethylformamide-water), washed with 10 ml water, 5 ml ethanol and 5 ml ether to give 0.3 g (49%) 1-benzyl-6-nitroquinoxaline-2,3(1H,4H)-dione. M.p. (DSC): 292.2° C. 1H-NMR (DMSO-d6): 12.4 (1H, broad s), 8.2-7.0 (8H, m), 5.4 (2H, s).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationwas filtered off
  3. washwashed with water
  4. customThe crude product was recrystallized (dimethylformamide-water)
  5. washwashed with 10 ml water, 5 ml ethanol and 5 ml ether

Sources & evidence

ORD record
ord-154b1c34f6774ceb9f431f719fa3ddad
Source dataset
uspto-grants-1991_06
Patent number
US05026704

Reaction notes

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