1-Naphthaleneacetonitrile → HCID 13980433, compound

To a stirred suspension of NH4Cl (1.6 g, 30 mmol) in anhydrous toluene (50 mL) was added trimethyl aluminium (2M in toluene, 15 mL, 30 mmol) at 0° C. The mixture was then warmed to room temperature and stirred for 2 h. A solution of 2-(naphthalen-1-yl)acetonitrile (1.67 g, 10 mmol) in toluene (10 mL) was added to the above reaction mixture and the reaction mixture was stirred at 80° C. for 18 h. After completion of the reaction, the reaction mixture was quenched with a suspension of silica gel in chloroform. The mixture was stirred at room temperature for 0.5 h before being filtered through a sintered funnel. The silica gel was washed with methanol. The combined filtrate was concentrated under reduced pressure to give the crude product as an off-white solid (2 g, 91%), which was used directly without further purification.

1. stirringthe reaction mixture was stirred at 80° C. for 18 h
2. customAfter completion of the reaction
3. customthe reaction mixture was quenched with a suspension of silica gel in chloroform
4. stirringThe mixture was stirred at room temperature for 0.5 h
5. filtrationbefore being filtered through a sintered funnel
6. washThe silica gel was washed with methanol
7. concentrationThe combined filtrate was concentrated under reduced pressure

ORD record

ord-51a1a775da9c4588a6853e16b34ffd23

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045486B2