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

HRID 1251142Notes

Reaction equation

HRID 1251142 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-537113f32c1f4ff7aba536679d106e75
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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