Ammonia → HCID 19363367, compound

4-[2-(6-Methoxy-1-oxo-5-pentyloxy-3,4-dihydro-1H-isoquinolin-2-yl)ethyl]phenyl acetate (720 mg, 1.69 mmol, 1 eq) was dissolved in methanol (10 ml), and aqueous ammonia (10 ml) was added. The mixture was stirred for 2 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and water (20 ml) was added to the residue. The mixture was extracted twice with ethyl acetate (30 ml). The organic layers were combined, washed with a 1N aqueous hydrochloric acid solution (10 ml) and saturated brine (50 ml), and dried over anhydrous sodium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1) to give 2-[2-(4-hydroxyphenyl)ethyl]-6-methoxy-5-pentyloxy-3,4dihydro-2H-isoquinolin-1-one (396 mg, 61.0%) as colorless crystals.

1. concentrationThe reaction mixture was concentrated under reduced pressure, and water (20 ml)
2. additionwas added to the residue
3. extractionThe mixture was extracted twice with ethyl acetate (30 ml)
4. washwashed with a 1N aqueous hydrochloric acid solution (10 ml) and saturated brine (50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. filtrationThe drying agent was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe obtained residue was purified by column chromatography on silica gel (ethyl acetate/hexane=1/1)

ORD record

ord-88a4058026cb426faef825887eb7ffd3

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919