Methanol → Isoquinoline-6-carboxaldehyde

Temperature

-78 °C

To a 150 mL round-bottomed flask was added 6-vinylisoquinoline (2.47 g, 16 mmol) and MeOH (35 mL)/DCM (35 mL). The resulting solution was cooled to −78° C. The reaction was ozonized until a blue color persisted, then nitrogen gas was bubbled through the solution for 15 minutes to purge the ozone. The reaction was then treated with solid sodium bicarbarbonate. (1.5 g) and dimethyl sulfide (3.2 mL, 0.2 mL/mmol of SM) and the mixture was warmed to room temperature and stirred overnight. The reaction mixture was diluted with water (100 mL) and extracted with DCM (3×75 mL). The combined organic layers were dried over Na2SO4, filtered, and the residue product isoquinoline-6-carbaldehyde (2.35 g, 94% yield) was used without further manipulation. LCMS (API-ES) m/z (%): 158.1 (100%, M++H).

1. customnitrogen gas was bubbled through the solution for 15 minutes
2. customto purge the ozone
3. additionThe reaction was then treated with solid sodium bicarbarbonate
4. temperature(1.5 g) and dimethyl sulfide (3.2 mL, 0.2 mL/mmol of SM) and the mixture was warmed to room temperature
5. additionThe reaction mixture was diluted with water (100 mL)
6. extractionextracted with DCM (3×75 mL)
7. dry with materialThe combined organic layers were dried over Na2SO4
8. filtrationfiltered

ORD record

ord-fd7334d1f8dd4f9791049e5168ac5b66

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897619B2