6-(Methanesulfonyloxymethyl)quinoline → 6-[(1H-Imidazol-1-YL)methyl]quinoline

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

The title product from Step A above was dissolved in anhydrous DMF (10 mL) and sodium imidazole (0.367 g, 4.08 mmoles) was added. The mixture was heated at 70° C. under argon for 2 h and then evaporated to dryness. The product was chromatographed on silica gel to give the title compound (0. 1559 g, 27%): FABMS: m/z 210.0 (MH+); δH (CDCl3) 5.34 (1H, s, CH2), 6.97 (1H, s, Im-H5), 7.15 (1H, s, Im-H4), 7.44 (1H, dd, Ar—H3), 7.52 (2H, m, Ar—H5 and Ar—H7), 7.64 (1H, s, Im-H2), 8.12 (2H, d, Ar—H4 and Ar—H8) and 8.95 ppm (1H, d, Ar—H2); δC (CDCI3) CH2: 50.6; CH: 119.4, 121.8, 125.9, 128.4, 130.1, 130.5, 136.0, 137.6, 151.0; C: 128.2, 134.6, 147.9.

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