反应详情

To a mixture of 5-chloromethyl-8-quinolinol hydrochloride, 11 (0.20 g, 0.86 mmol) and diisopropylethylamine (0.3 mL, 1.73 mmol, 2.2 equiv) in 25 mL CHCl3 at 0° C. was added 9a (0.25 g, 0.78 mmol). The mixture was stirred for 24 h at room temperature. CHCl3 (100 mL) was added and the solution obtained was washed with 10% NaHCO3, brine, and then dried over Na2SO4. The solution was filtered and evaporated to dryness. The residue was made hydrochloride salt and crystallized from ethanol to yield 12a as yellow solid (0.28 g, 57.3%). 1H NMR of HCl salt (400 MHz, DMSO-d6) δ ppm 0.88-0.99 (m, 3H), 1.79-1.81 (bs, 4H), 2.298 (bs, 1H), 2.476-2.48 (m, 2H), 2.74 (s, 2H), 2.96-3.02 (t, 1H, J=12 Hz), 3.122 (bs, 3H), 3.34-3.65 (m, 12H), 6.51-6.56 (m, 2H), 6.86-6.88 (d, 1H, J=8 Hz), 7.50-7.52 (d, 1H, J=8 Hz), 7.997-8.008 (m, 2H); 9.06-9.07 (d, 1H, J=4 Hz); 9.49-9.51 (d, 1H, J=8 Hz). The hydrochloride salt mp 242-242° C. Analysis calculated for (C29H40.6N4O3.3, 4HCl) C, H, N.

1. customthe solution obtained
2. washwas washed with 10% NaHCO3, brine
3. dry with materialdried over Na2SO4
4. filtrationThe solution was filtered
5. customevaporated to dryness
6. customcrystallized from ethanol