Potassium Hydroxide → HCID 9952547, compound

Participants

Reaction Conditions

Reaction Steps

A solution 4-[(1-isopropyl-4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-propyl-amino]-benzoic acid ethyl ester (Compound 49, 12.0 mg, 0.0284 mmol) in ethanol (1 mL) was treated with 2N KOH (0.5 mL) and stirred at 50° C. for 2 days. The solvent was removed under reduced pressure and the residue was washed with ethyl acetate and acidified with 2N HCl. The aqueous layer was extracted with ethyl acetate and the combined organic layers were dried with MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexane, Rf=0.28) to give the title compound (11 mg, 98%) as a white solid: 1H NMR (300 MHz, CDCl3): δ0.95 (t, 3 H, J=7.4 Hz), 1.16 (d, 6 H, J=6.6 Hz), 1.31 (s, 6 H), 1.69-1.80 (m, 4 H), 1.95 (s, 3 H), 3.15 (t, 2 H, J=5.9 Hz), 3.54 (br s, 2 H), 3.97 (sp, 1 H, J=6.6 Hz), 6.47 (d, 2 H, J=8.9 Hz), 7.08 (s, 1 H), 7.88 (d, 2 H, J=8.9 Hz).

Provenance & Evidence