Ammonia → 6,8-Difluoro-3-methylisoquinoline

Reaktionsgleichung

[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([C:11]#[C:12][CH3:13])[C:3]=1[CH:4]=O.[NH3:14].CO>>[F:10][C:8]1[CH:7]=[C:6]2[C:3](=[C:2]([F:1])[CH:9]=1)[CH:4]=[N:14][C:12]([CH3:13])=[CH:11]2

Komponenten

Edukt 3

HCID 222Ammonia

HCID 887Methanol

HCID 858697692,4-Difluoro-6-prop-1-ynylbenzaldehyde

Produkt 1

HCID 691593316,8-Difluoro-3-methylisoquinolineAusbeute 59 %

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 2,4-difluoro-6-prop-1-ynylbenzaldehyde (Description 71, 8.7 g; 48.8 mmol) and 2.0M ammonia in methanol (244 ml; 488 mmol) were heated together at 80° C. in a Parr apparatus (approx 35 psi achieved) for 5 hours. The cooled mixture was evaporated and the residue purified by column chromatography on silica-elution with 100% dichloromethane to give the title compound (5.2 g, 59%) as a brown solid.