Potassium Carbonate → 7-Methoxy-3-phenylisoquinoline-2-oxide

HRID 1006909Notes

Reaction equation

HRID 1006909 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:10]=2[CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:18][O:17][C:14]1[CH:13]=[C:10]2[C:9]([CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N+:20]([O-:21])=[CH:11]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 225029022-(2-Phenylethynyl)-5-methoxybenzaldehyde

Product 1

HCID 225030267-Methoxy-3-phenylisoquinoline-2-oxideYield 58.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-(2-Phenylethynyl)-5-methoxybenzaldehyde (0.48 g) was reacted with hydroxylamine hydrochloride (0.17 g) and sodium acetate (0.21 g) in ethanol (10 ml) at 60° C. for 2 hr. Potassium carbonate (0.3 g) and water (1 ml) were added to the reaction mixture, and it was heated under reflux for 12 hr. The reaction solution was evaporated. The resulting residue was extracted with methylene chloride, and then washed with brine and dried. The solvent was removed, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give 0.30 g of the title compound as a yellowish brown amorphous.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hr
  3. customThe reaction solution was evaporated
  4. extractionThe resulting residue was extracted with methylene chloride
  5. washwashed with brine
  6. customdried
  7. customThe solvent was removed
  8. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-0fc8d4ccb0c749719250653c55d08973
Source dataset
uspto-grants-2004_09
Patent number
US06790844B2

Reaction notes

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