Diphenylmethane → 6-methoxyisoquinolin-1(2H)-one

Temperature

23 °C

Ethyl chloroformate (4.3 mL, 44.5 mmol) was added drop wise at 0° C. to a solution of 3-methoxycinnamic acid (5.3 g, 29.7 mmol) and triethylamine (8.3 mL, 59.4 mmol) in acetone (35 mL). After 1 hour at 0° C., aqueous sodium azide (3.1 g, 47.5 mmol, 16 mL water) was added drop wise, and the reaction mixture was stirred at 23° C. for 16 hours. Water (50 mL) was added to the mixture and the volatile removed under reduced pressure. The resulting slurry was extracted with toluene (3×25 mL) and the combined organic layers were dried over magnesium sulfate. The dried solution was filtered and added dropwise to a solution of diphenylmethane (25 mL) and tributylamine (14.2 mL, 59.4 mmol) at 190° C. The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210° C. for 2 hours. After cooling, the precipitated product was collected by filtration, washed with hexanes, and dried under vacuum to yield 6-methoxyisoquinolin-1(2H)-one (1.7 g, 9.7 mmol, 33% yield). MS m/z 176 (M++H).

1. customthe volatile removed under reduced pressure
2. extractionThe resulting slurry was extracted with toluene (3×25 mL)
3. dry with materialthe combined organic layers were dried over magnesium sulfate
4. filtrationThe dried solution was filtered
5. distillationThe toluene was distilled off
6. additionas added
7. additionAfter complete addition
8. temperaturethe reaction temperature was raised to 210° C. for 2 hours
9. temperatureAfter cooling
10. filtrationthe precipitated product was collected by filtration
11. washwashed with hexanes
12. customdried under vacuum

ORD record

ord-b7d6a0a27a6d4eba8a5f505e2ad14ef8

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08211897B2