Reaction #2069943

Reaction equation

compound

(4-Butylphenyl)(1-isoquinolyl)ketone

hydrazine monohydrate

potassium hydroxide

→

title compound

Yield 55.3%

1-(4-butylbenzyl)isoquinoline

Yield 55.3%

Solvents

diethylene glycol

Conditions

Workup

1. 1
   workup.WAITat 200° C. for 1 hour
2. 2
   TemperatureThe mixture was cooled to room temperature
3. 3
   Extractionthis was extracted with ethyl acetate
4. 4
   WashThe extract was washed with water
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography

Procedure

The compound of Example B3 (1.7 g, 6.0 mmol), hydrazine monohydrate (836 mg, 17 mmol), and potassium hydroxide (769 mg, 14 mmol) were added to diethylene glycol (8.5 ml), and this mixture was stirred at 80° C. for 1 hour, at 160° C. for 3.5 hours, then at 200° C. for 1 hour. The mixture was cooled to room temperature, ice water was added, and this was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (914 mg).

Source