O-Methylhydroxylamine → HCID 88124618, compound

HRID 1464613Notes

Reaction equation

HRID 1464613 reaction equation
[C:1]([CH2:9][N:10]1[CH2:15][CH2:14][N:13]([C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]3)=[O:17])[CH2:12][CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:29](N)[CH3:30].[C:32]([O-:35])(=[O:34])C.[Na+].Cl.[O:38]([NH2:40])[CH3:39]>C(O)C.O>[C:30]([OH:29])(=[O:8])[C:32]([OH:35])=[O:34].[C:2]1([C:1](=[N:40][O:38][CH3:39])[CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[NH:24][C:23](=[O:28])[CH2:22][CH2:21]4)=[O:17])[CH2:12][CH2:11]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 4113O-MethylhydroxylamineHCID 517045Sodium Acetate2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 13369791HCID 13369791, compound

Product 1

HCID 88124618HCID 88124618, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2 Grams of 6-[4-(benzoylmethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril, 0.53 g of methoxylamine and 0.78 g of sodium acetate were dissolved in 10 ml of ethanol and 5 ml of water, then the solution was refluxed for 4 hours with stirring. Further, 0.53 g of methoxylamine hydrochloride and 0.78 g of sodium acetate were added to the reaction mixture, and refluxed for 2 hours with stirring. After the reaction was completed, the solvent was removed by evaporation under reduced pressure. Thus obtained resIdue was extracted with chloroform, and the extract was dried with anhydrous sodium carbonate, then the solvent was removed by evaporation. The residue thus obtained was purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1) then the desired compound was converted into an oxalate by adding with oxalic acid in acetone, and recrystallized from ethanol-water to yield 2.6 g of 6- [4-(2-phenyl-2-methoxyiminoethyl)-1-piperazinylcarbonyl]-3,4-dihydrocarbostyril oxalate. White powdery substance. Melting point: 203°-205° C. (decomp.).

Workup

  1. temperaturerefluxed for 2 hours
  2. stirringwith stirring
  3. customthe solvent was removed by evaporation under reduced pressure
  4. extractionThus obtained resIdue was extracted with chloroform
  5. dry with materialthe extract was dried with anhydrous sodium carbonate
  6. customthe solvent was removed by evaporation
  7. customThe residue thus obtained
  8. customwas purified by means of a silica gel column chromatography (eluent: dichloromethane:methanol=50:1)
  9. additionby adding with oxalic acid in acetone
  10. customrecrystallized from ethanol-water

Sources & evidence

ORD record
ord-bba6293533ee4ecb8941e97827f548ad
Source dataset
uspto-grants-1994_04
Patent number
US05306719

Reaction notes

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