Acetone → HCID 19363284, compound

Participants

Reaction Steps

3-(3-Methoxy-2-pentyloxyphenyl)propionic acid (1.00 g, 3.75 mmol), thionyl chloride (0.72 ml, 10 mmol) and one drop of DMF were mixed, and the mixture was stirred at room temperature for 15 minutes. Toluene (10 ml) was added and the mixture was filtered. The filtrate was concentrated under reduced pressure. Acetone (5 ml) and a solution of sodium azide (0.33 g, 5.0 mmol) in water (0.5 ml) were added to the obtained residue, and the mixture was stirred at room temperature for 20 minutes. Water (5 ml) was add, and the aqueous layer was extracted twice with toluene (20 ml). The organic layers were combined, washed twice with saturated brine (10 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Toluene (10 ml) was added to the obtained residue. The mixture was refluxed under heating for 2.5 hours, and toluene was evaporated under reduced pressure. Polyphosphoric acid (3 ml) was added to the obtained residue and the mixture was stirred for 40 minutes. Water (20 ml) and ethyl acetate (50 ml) were added to separate the organic layer. The organic layer was washed successively with water (10 ml) and saturated brine (10 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. Hexane (10 ml) was added to the obtained residue, and the precipitated crystals were collected by filtration to give 6-methoxy-5-pentyloxy-3,4-dihydro-2H-isoquinolin-1-one (829 mg, 84%) as colorless needles.

Provenance & Evidence