1,2,3,4-Tetrahydroquinoline → 4-Bromo-3-(3,4-dihydro-2H-quinoline-1-carbonyl)-benzonitrile

Participants

Reaction Steps

To a solution of 2-bromo-5-cyano-benzoic acid (0.50 g, 2.12 mmol, 1.0 equiv; [CAS RN 845616-12-8]) in dichloromethane (5 mL) was added 1,2,3,4-tetrahydro-quinoline (0.35 g, 330 μL, 2.66 mmol, 1.2 equiv; [CAS RN 635-46-1]), N-ethyldiisopropylamine (1.43 g, 1.88 mL, 11.06 mmol, 5.0 equiv; [CAS RN 7087-68-5]) and 2-chloro-1-methylpyridinium iodide (0.68 g, 2.66 mmol, 1.2 equiv; [CAS RN 14338-32-0]). The reaction mixture was stirred at rt over the weekend. To the residue was added a sat. solution of NaHCO3 (100 mL) and the solution extracted with dichloromethane (3×50 mL). The combined organic phases were dried over Na2SO4 and the product purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of toluene/acetone affording 0.35 g (46%) of the title compound as a light yellow solid. MS (ISP): 341.1 [M+H]+.

Provenance & Evidence