ChemicalBook CAS DataBase List 6-Isoquinolinecarboxaldehyde (9CI)

6-Isoquinolinecarboxaldehyde (9CI) synthesis

6synthesis methods

Product Name:6-Isoquinolinecarboxaldehyde (9CI)
CAS Number:173089-81-1
Molecular formula:C10H7NO
Molecular Weight:157.17

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Yield: 94%

Reaction Conditions:

Stage #1:6-vinylisoquinoline with ozone in methanol;dichloromethane at -78; for 0.25 h;
Stage #2: with dimethylsulfide;sodium hydrogencarbonate in methanol;dichloromethane at 20;

Steps:

6; 4
[00212] Isoquinoline-6-carbaldehyde: 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 x 75 mL). The combined organic layers were dried over Na₂SO^ 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%, M⁴H-H).

References:

AMGEN INC. WO2009/11880, 2009, A2 Location in patent:Page/Page column 100-101

34784-05-9 Synthesis