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Hydroxylamine HCl → 1-Ethoxycarbonylmethyl-7-(3-hydroxyiminomethyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

HRID 1458874
Notes
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Reaction equation

HRID 1458874 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-].[OH:31][NH3+:32].C([O-])(=O)C.[Na+]>O.CCO>[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]=[N:32][OH:31])=[CH:18]3)[CH:15]=2)[NH:10][C:9](=[O:28])[C:8]1=[O:29])=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 153379971-(Ethoxycarbonylmethyl)-7-(3-formyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedione

Product 1

HCID 542796031-Ethoxycarbonylmethyl-7-(3-hydroxyiminomethyl-1-pyrrolyl)-6-trifluoromethyl-2,3(1H,4H)-quinoxalinedioneYield 130%

Reagents, catalysts & solvents 1

HCID 19096565
Water ethanol
Solvent

Procedure

1.2 g (2.9 mmol) of the compound from Example 70, 0.4 g (6 mmol) of hydroxylammonium chloride and 0.48 g (6 mmol) of sodium acetate in 45 ml of H2O/EtOH (2:1) were refluxed for 30 minutes. The organic solvent was removed under reduced pressure, and the resulting aqueous phase was extracted with ethyl acetate. The organic phase was dried and concentrated under reduced pressure. The residue was recrystallized from ethanol to yield 1.6 g (70%) of the product. Melting point >250° C.

Workup

  1. customThe organic solvent was removed under reduced pressure
  2. extractionthe resulting aqueous phase was extracted with ethyl acetate
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-953068f96e9e4c6fa64936f7626fc009
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05852017

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes