Phosphorus oxychloride → 1-Chloro-3-(3-methoxyphenyl)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:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)C#N.P(Cl)(Cl)([Cl:24])=O>>[Cl:24][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:19]=[CH:16][CH:15]=[C:14]([O:13][CH3:12])[CH:21]=2)[N:2]=1Participants
Procedure
3-(4-Methoxyphenyl)isoquinone-1-one obtained by reacting N-methyl-o-toluamide (1.49 g) and 3-methoxybenzonitrile (1.33 g) according to Example 10-1 was reacted with phosphorus oxychloride (10 ml) according to Example 10-2, to give 1-chloro-3-(3-methoxyphenyl)isoquinoline. Then, it was reacted with N-ethylpiperazine (10 ml) at 120° C. for 6 hr. The reaction solution was evaporated, and ethyl acetate and water were added to the resulting residue. 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-f4023905465c4477ae8e9bb2bd30f7e1
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06875761B2
Reaction notes
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