Acetone → HCID 19363284, compound

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.

1. filtrationthe mixture was filtered
2. concentrationThe filtrate was concentrated under reduced pressure
3. stirringthe mixture was stirred at room temperature for 20 minutes
4. extractionthe aqueous layer was extracted twice with toluene (20 ml)
5. washwashed twice with saturated brine (10 ml)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationThe drying agent was filtered off
8. concentrationthe filtrate was concentrated under reduced pressure
9. additionToluene (10 ml) was added to the obtained residue
10. temperatureThe mixture was refluxed
11. temperatureunder heating for 2.5 hours
12. customtoluene was evaporated under reduced pressure
13. additionPolyphosphoric acid (3 ml) was added to the obtained residue
14. stirringthe mixture was stirred for 40 minutes
15. additionWater (20 ml) and ethyl acetate (50 ml) were added
16. customto separate the organic layer
17. washThe organic layer was washed successively with water (10 ml) and saturated brine (10 ml)
18. dry with materialdried over anhydrous magnesium sulfate
19. filtrationThe drying agent was filtered off
20. concentrationthe filtrate was concentrated under reduced pressure
21. additionHexane (10 ml) was added to the obtained residue
22. filtrationthe precipitated crystals were collected by filtration

ORD record

ord-52d67136781249fd919d58a0de2e9fac

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919