Acetic Acid → HCID 19101562, compound

HRID 1974488Notes

Reaction equation

HRID 1974488 reaction equation
[ClH:1].Cl.[N:3]1([C:8]2[C:14]([N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)=[CH:13][C:11]([NH2:12])=[C:10]([N+:20]([O-])=[O:21])[CH:9]=2)[CH:7]=[CH:6][N:5]=[CH:4]1.[C:23]([OH:26])(=[O:25])[CH3:24].C[OH:28]>[Pd]>[OH2:21].[OH2:25].[ClH:1].[ClH:1].[N:3]1([C:8]2[CH:9]=[C:10]3[C:11](=[CH:13][C:14]=2[N:15]2[CH:19]=[CH:18][N:17]=[CH:16]2)[NH:12][C:24](=[O:28])[C:23](=[O:26])[NH:20]3)[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 19101611HCID 19101611, compound

Product 1

HCID 19101562HCID 19101562, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 1 g of 4,5-di-(1-imidazolyl)-2-nitroaniline dihydrochloride, 5 ml of acetic acid, 5 ml of methanol and 0.1 g of 10% palladium-on-carbon was subjected to hydrogenation reaction. The reaction mixture was filtered and the filtrate was washed with hydrochloric acid and concentrated under reduced pressure. The concentrate was dissolved in 350 mg oxalic acid-6 ml of 4N-hydrochloric acid and the solution was subjected to dry distillation overnight. The resulting crystals were recovered by filtration and recrystallized from 4N-hydrochloric acid to provide 170 mg of 6,7-di-(1-imidazolyl)quinoxaline-2,3-(1H,4H)-dione dihydrochloride dihydrate.

Workup

  1. customwas subjected to hydrogenation reaction
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with hydrochloric acid
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe concentrate was dissolved in 350 mg oxalic acid-6 ml of 4N-hydrochloric acid
  6. customto dry
  7. distillationdistillation overnight
  8. filtrationThe resulting crystals were recovered by filtration
  9. customrecrystallized from 4N-hydrochloric acid

Sources & evidence

ORD record
ord-ed8c914207d544c5bbaba91ff7507067
Source dataset
uspto-grants-1994_02
Patent number
US05283244

Reaction notes

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