Phosphorus oxychloride → 1-Chloro-3-(4-trifluoromethoxyphenyl)isoquinoline

HRID 1251206Notes

Reaction equation

[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12](=O)[C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][CH:5]=1.P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([O:3][C:2]([F:22])([F:21])[F:1])=[CH:5][CH:6]=2)[N:11]=1

Participants

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 225032223-(4-Trifluoromethoxyphenyl)isoquinolin-1-one

Product 1

HCID 225028651-Chloro-3-(4-trifluoromethoxyphenyl)isoquinoline

Procedure

The resulting 3-(4-trifluoromethoxyphenyl)isoquinolin-1-one (3.01 g) was reacted with phosphorus oxychloride (20 ml) according to the method of Example 10-2, to give 1-chloro-3-(4-trifluoromethoxyphenyl)isoquinoline, which was then reacted as it was with N-ethylpiperazine (40 ml) at 90° C. overnight. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system), to give 3.65 g of the free compound of the title compound as a pale yellow oil.

Sources & evidence

ORD record: ord-85eb97423aba4a1da1e34c8c940b5f41
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06340759B1

Reaction notes

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