Water → HCID 9794709, compound

HRID 1387206Notes

Reaction equation

HRID 1387206 reaction equation
C([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[O:29])[NH:20][O:21]CC3C=CC=CC=3)[CH:17]=2)[NH:12][C:11](=[O:30])[C:10]1=[O:31])C1C=CC=CC=1.O.[OH-].[Na+]>C(O)C.[Pd]>[OH:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[O:29])[NH:20][OH:21])[CH:17]=2)[NH:12][C:11](=[O:30])[C:10]1=[O:31]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 18415562HCID 18415562, compound

Product 1

HCID 9794709HCID 9794709, compoundYield 76.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-Benzyloxy-7-(benzyloxycarbamoyl)quinoxaline-2,3(1H,4H)-dione (250 mg, 0.6 mmol) in 50 ml of ethanol was hydrogenated at atmospheric pressure and room temperature for 1 h in the presence of 50 mg of 5% palladium on carbon. Water (20 ml) and 4 ml of 2 N sodium hydroxide was added to dissolve the product and the catalyst was removed by filtration. The filtrate was acidified with 4 ml of 4M hydrochloric acid, evaporated to about 10 ml and filtered to give a white solid. Washing with a small amount of cold water and ethanol yielded 109 mg (70%) of the title compound. 1H-NMR (DMSO-d6): 7.21 (d, J=8 Hz, 1H, ArH), 7.60 (dd, J=8 Hz, 2 Hz, 1H, ArH), 7.90 (d, J=2 Hz, 1H, ArH), 9.05 (br.s, 1H, exchangeable), 11.35 (br.s, 1H, exchangeable), 11.82 (br.s, 1H, exchangeable), 12.35 (br.s, 1H, exchangeable).

Workup

  1. dissolutionto dissolve the product
  2. customthe catalyst was removed by filtration
  3. customevaporated to about 10 ml
  4. filtrationfiltered
  5. customto give a white solid
  6. washWashing with a small amount of cold water and ethanol

Sources & evidence

ORD record
ord-6f2f25c942784e008cc49af7e6e8e702
Source dataset
uspto-grants-2001_07
Patent number
US06268163B1

Reaction notes

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