Phosphorus oxychloride → 1-Chloro-3-(2,5-dimethoxyphenyl)isoquinoline
Reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:6]([CH3:11])=[CH:7][CH:8]=[CH:9][CH:10]=1)=O.[CH3:12][O:13][C:14]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:15]=1C#N.P(Cl)(Cl)([Cl:26])=O>>[Cl:26][C:3]1[C:5]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:11]=[C:1]([C:20]2[CH:21]=[C:14]([O:13][CH3:12])[CH:15]=[CH:18][C:19]=2[O:22][CH3:23])[N:2]=1Participants
Procedure
3-(2,5-Dimethoxyphenyl)isoquinolin-1-one (0.61 g) obtained by reacting N-methyl-o-toluamide (1.64 g) and 2,5-dimethoxybenzonitrile (1.80 g) according to Example 10-1 was reacted with phosphorous oxychloride (10 ml) according to Example 10-2, to give 1-chloro-3-(2,5-dimethoxyphenyl)isoquinoline, which was then reacted with N-ethylpiperazine (15 ml) at 100° C. for 8 hr. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The resulting organic layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the free compound of the title compound as a pale yellow oil.
Sources & evidence
- ORD record
- ord-da7efd7f792f437392d54fb81ba6a728
- Source dataset
- uspto-grants-2002_01
- Patent number
- US06340759B1
Reaction notes
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