Sodium Acetate → 7-(3-Benzyloxyiminomethyl-1-pyrrolyl)-1-(ethoxycarbonylmethyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 861537Notes

Reaction equation

HRID 861537 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:24]([F:27])([F:26])[F:25])=[C:14]([N:17]3[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18]3)[CH:15]=2)[NH:10][C:9](=[O:28])[C:8]1=[O:29])=[O:5])[CH3:2].[Cl-].[CH2:31]([O:38][NH3+:39])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C([O-])(=O)C.[Na+]>CCO.O>[CH2:31]([O:38][N:39]=[CH:22][C:19]1[CH:20]=[CH:21][N:17]([C:14]2[CH:15]=[C:16]3[C:11]([NH:10][C:9](=[O:28])[C:8](=[O:29])[N:7]3[CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:12][C:13]=2[C:24]([F:26])([F:27])[F:25])[CH:18]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 11094915o-Benzylhydroxylammonium chlorideHCID 153379971-(Ethoxycarbonylmethyl)-7-(3-formyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 545666627-(3-Benzyloxyiminomethyl-1-pyrrolyl)-1-(ethoxycarbonylmethyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 84%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

1.1 g (2.7 mmol) of the compound of Example 70, 0.86 g (5.4 mmol) of O-benzylhydroxylammonium chloride and 0.44 g (5.4 mmol) of sodium acetate in 4.5 ml of EtOH/H2O (1:2) were refluxed for 30 minutes. The ethanol was then removed under reduced pressure, and the precipitate was filtered off with suction and recrystallized from ethanol to yield 1.15 g (84%) of the product. The 1H-NMR shows that an E/Z mixture is present. Melting point 142°-147° C.

Workup

  1. customThe ethanol was then removed under reduced pressure
  2. filtrationthe precipitate was filtered off with suction
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-5fa08d793abb4083ba05527ace9703b3
Source dataset
uspto-grants-1998_02
Patent number
US05714489

Reaction notes

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