Oxalic acid dihydrate → HCID 19827809, compound

HRID 1709197Notes

Reaction equation

HRID 1709197 reaction equation
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=2[NH2:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[C:20](O)(=[O:24])[C:21](O)=[O:22]>Cl>[CH:1]1([N:7]2[C:8]3[C:9](=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=3)[NH:17][C:21](=[O:22])[C:20]2=[O:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 4321269HCID 4321269, compound

Product 1

HCID 19827809HCID 19827809, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 0,9 g (3,1 mmol) N-cyclohexyl-2-amino-4-nitroaniline and 1,0 g (7, 9 mmol) oxalic acid dihydrate in 50 ml 4 N hydrochloric acid was refluxed for 5 h. After cooling to 25° C. the product was filtered off. The crude product was recrystallized (ether-water) to give 0,2 g (19%) 1-cyclo-hexyl-6-nitroquinoxaline-2,3(1H,4H)-dione. M.p. (DSC): decomp. 1H-NMR (DMSO-d6): 12.2 (1H, broad s), 8.1-7.7 (3H, m), 3.0-1.0 (11H, m).

Workup

  1. temperaturewas refluxed for 5 h
  2. filtrationwas filtered off
  3. customThe crude product was recrystallized (ether-water)

Sources & evidence

ORD record
ord-807505ac4e9a4e1eba83b0d65551b614
Source dataset
uspto-grants-1990_08
Patent number
US04948794

Reaction notes

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