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-methoxy cinnamic acid (5.3 g, 29.7 mmol) and triethylamine (8.3 mL, 59.4 mmol) in acetone (35 mL). After 1 h 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 h. Water (50 mL) was added to the mixture and the volatile was removed under vacuo. The resulting slurry was extracted with toluene (3×25 mL) and the combined organic layers were dried (MgSO4). The dried solution was filtered and added drop wise at 190° C. to a solution of diphenylmethane (25 mL) and tributylamine (14.2 mL, 59.4 mmol). The toluene was distilled off as added. After complete addition, the reaction temperature was raised to 210° C. for 2 h. After cooling, the precipitated product was collected by filtration and washed with hexanes and dried under vacuum to yield 6-Methoxy-2H-isoquinolin-1-one (1.7 g, 9.7 mmol, 33% yield). MS m/z 176 (M++H).

1. customthe volatile was removed under vacuo
2. extractionThe resulting slurry was extracted with toluene (3×25 mL)
3. dry with materialthe combined organic layers were dried (MgSO4)
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 h
9. temperatureAfter cooling
10. filtrationthe precipitated product was collected by filtration
11. washwashed with hexanes
12. customdried under vacuum

ORD record

ord-a059590700164b7e9247d73e00c721d6

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518874B2