Potassium Carbonate → 7-Methoxy-3-(2-methoxyphenyl)isoquinoline-2-oxide
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]#[C:10][C:11]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:12]=1[CH:13]=O.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH3:20][O:19][C:16]1[CH:15]=[C:12]2[C:11]([CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N+:22]([O-:23])=[CH:13]2)=[CH:18][CH:17]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
2-[2-(2-Methoxyphenyl)ethynyl]-5-methoxybenzaldehyde (0.95 g), hydroxylamine hydrochloride (0.25 g) and sodium acetate (0.32 g) were reacted in ethanol (20 ml) at 60° C. for 2 hr. Potassium carbonate (0.6 g) and water (2 ml) were added to the reaction mixture, and the mixture was heated under reflux for 12 hr. The reaction solution was evaporated, and then the resulting residue was extracted with methylene chloride, 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 0.60 g of the title compound as a yellowish brown amorphous.
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 12 hr
- customThe reaction solution was evaporated
- extractionthe resulting residue was extracted with methylene chloride
- washwashed with brine
- customdried
- customThe solvent was removed
- customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)
Sources & evidence
- ORD record
- ord-1e46871c3f964ec4940e80ac2e688282
- Source dataset
- uspto-grants-2004_09
- Patent number
- US06790844B2
Reaction notes
Loading…