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

HRID 1251206Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251206
[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

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 225032223-(4-Trifluoromethoxyphenyl)isoquinolin-1-one

Produkt 1

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

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-85eb97423aba4a1da1e34c8c940b5f41
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340759B1

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