Methanol → HCID 178502640, compound

HRID 423190Notes

Reaction equation

HRID 423190 reaction equation
CO.[CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:14]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[C:13]([OH:32])[C:12]2=[O:33])=[CH:7][CH:6]=1)=O.[Cl-].[CH3:35][O:36][NH3+:37].C([O-])(=O)C.[Na+]>O>[OH:32][C:13]1[C:12](=[O:33])[N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:3]=[N:37][O:36][CH3:35])=[CH:10][CH:9]=2)[CH:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:14]=1[C:22](=[O:31])[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11639O-methylhydroxylammonium chlorideHCID 517045Sodium AcetateHCID 178491320HCID 178491320, compound

Product 1

HCID 178502640HCID 178502640, compoundYield 3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the 0.1M methanol solution of 1-(4-formylphenyl)-3-hydroxy-4-(4-methoxybenzoyl)-5-phenyl-1,5-dihydropyrrol-2-one (1 mL, 0.1 mmol) was added O-methylhydroxylammonium chloride (0.025 g, 0.3 mmol) and sodium acetate (0.025 g, 0.3 mmol). The mixture was stirred under reflux for 3 hr. Water (50 mL) was added to the mixture, which was then extracted with ethyl acetate (50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the precipitate was collected by filtration and dried to give 3-hydroxy-4-(4-methoxybenzoyl)-1-(4-methoxyiminomethylphenyl)-5-phenyl-1,5-dihydro-pyrrol-2-one (1.3 mg, 3%) as slightly yellow crystals.

Workup

  1. temperatureunder reflux for 3 hr
  2. extractionwas then extracted with ethyl acetate (50 mL)
  3. washThe organic layer was washed with brine (50 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate
  7. filtrationthe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-10188206180b42c4bceeae1dcbb4d1e4
Source dataset
uspto-grants-2012_01
Patent number
US08101644B2

Reaction notes

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