1-Benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-7-trifluoromethylquinoxalin-2(1H)-one → 3-[2-[(Diethoxyphosphoryl)acetyl]hydrazino]-1-hydroxy-7-trifluoromethylquinoxalin-2(1H)-one

HRID 744014Notes

Reaction equation

HRID 744014 reaction equation
C([O:8][N:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=2)[N:12]=[C:11]([NH:23][NH:24][C:25](=[O:35])[CH2:26][P:27]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])=[O:28])[C:10]1=[O:36])C1C=CC=CC=1>C(O)C.[Pd]>[CH2:33]([O:32][P:27]([CH2:26][C:25]([NH:24][NH:23][C:11]1[C:10](=[O:36])[N:9]([OH:8])[C:18]2[C:13]([N:12]=1)=[CH:14][CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=2)=[O:35])([O:29][CH2:30][CH3:31])=[O:28])[CH3:34]

Participants

4

Reactant 1

HCID 194214131-Benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-7-trifluoromethylquinoxalin-2(1H)-one

Product 1

HCID 194214493-[2-[(Diethoxyphosphoryl)acetyl]hydrazino]-1-hydroxy-7-trifluoromethylquinoxalin-2(1H)-oneYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-benzyloxy-3-[2-[(diethoxyphosphoryl)acetyl]hydrazino]-7-trifluoromethylquinoxalin-2(1H)-one (5.28 g, 10 mmol) in 500 ml of ethanol was hydrogenated at atmospheric pressure and room temperature for 1 h in the presence of 250 mg of 5% palladium on carbon. The catalyst was removed by filtration, and the filtrate was evaporated to dryness. The residue was triturated with ether and light petroleum to give 4.0 g (91%) of the title compound. M.p. 193°-196° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated to dryness
  3. customThe residue was triturated with ether and light petroleum

Sources & evidence

ORD record
ord-7a0252f92f204c62bc87b4baccdeadb4
Source dataset
uspto-grants-1996_09
Patent number
US05559106

Reaction notes

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