N,N'-Dimethylethylenediamine → 3-Quinolinecarbonitrile

Temperature

110 °C

An oven dried screw cap test tube was charged with NaCN (98 mg, 2.0 mmol), dried KI (32 mg, 0.168 mmol, 20 mol %) and CuI (56 mg, 0.337 mmol, 10 mol %), evacuated and backfilled with argon three times. 3-Bromoquinoline (225 μL, 1.66 mmol), N,N′-dimethylethylenediamine (180 μL, 1.69 mmol) and anhydrous toluene (1 mL) were added under argon. The tube was sealed and the reaction mixture was stirred magnetically at 110° C. for 24 h. The resulting yellow suspension was cooled to room temperature, 2 mL of ethyl acetate, 1 mL of ammonium hydroxide (30%) and 1 mL of water were added. The mixture was stirred at 25° C. for 10 min, then the organic layer was separated and the aqueous layer was extracted three times with ethyl acetate (3×2 mL). The combined organic layers were washed with 5 mL of water and dried over MgSO4. The solvent was removed at reduced pressure. Purification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1) provided 188 mg (74% yield) of the title compound as a white solid.

1. customAn oven dried screw
2. customcap test tube
3. customevacuated
4. customThe tube was sealed
5. temperatureThe resulting yellow suspension was cooled to room temperature
6. stirringThe mixture was stirred at 25° C. for 10 min
7. customthe organic layer was separated
8. extractionthe aqueous layer was extracted three times with ethyl acetate (3×2 mL)
9. washThe combined organic layers were washed with 5 mL of water
10. dry with materialdried over MgSO4
11. customThe solvent was removed at reduced pressure
12. customPurification of the residue by flash chromatography on silica gel (2×15 cm; hexane/ethyl acetate 10:1)

ORD record

ord-a4a875b8942a4292ba5345361ed13c40

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06888032B2