Potassium Hydroxide → HCID 90016528, compound

Participants

Reaction Steps

To the solution of 2-carbethoxy-8-m-tolyl-5-n-octyl-1,2,3,4-tetrahydropyrido[4,3-b]indole (7) in ethanol was added the aqueous solution of potassium hydroxide. The mixture was refluxed for 16 h. The reaction mixture was concentrated to remove ethanol and extracted with DCM for three times (15 mL×3). The DCM layer was washed with brine, dried with Na2SO4, filtered and concentrated to give brow residue. This residue was purified by silica gel column chromatography to give yellow oil. Yield: 63.6%. 1H NMR (300 Hz, CDCl3) δ 7.62 (br, 1H), 7.48-7.41 (m, 3H), 7.36-7.32 (m, 2H), 7.15-7.12 (m, 1H), 4.12 (br, 2H), 3.99 (t, 2H, J=7.2 Hz), 3.31 (br, 2H), 2.91 (br, 1H), 2.79 (br, 2H), 2.45 (s, 3H), 1.77-1.73 (m, 2H), 1.32-1.28 (s, 10H), 0.90 (t, 3H, J=6.6 Hz). 13C NMR (75 Hz, CDCl3) δ 142.57, 138.05, 135.45, 133.83, 132.48, 128.46, 128.06, 126.89, 125.91, 124.37, 120.56, 116.20, 109.13, 108.09, 43.26, 43.01, 42.14, 31.75, 30.35, 29.28, 29.14, 27.05, 23.10, 22.56, 21.55, 14.03.

Provenance & Evidence