Sodium Hydroxide → 4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]benzoic acid

Participants

Reaction Steps

A mixture of 4-[3-Methyl-1-(7-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester (48 mg, 0.13 mM) and 1N aqueous NaOH solution (0.318 mL, 0.318 mM) in THF-MeOH (1:1, 1.5 mL) was heated to 50° for 5 h. The reaction was cooled, concentrated to remove organic solvent. The aqueous solution was diluted with DCM (5 mL), acidified by 1N HCl solution to pH=3-4. The organic solution was separated and the aqueous solution was extracted with DCM (3×5 mL). The combined organic solution were dried (Na2SO4) and concentrated to give a yellow solid product (44 mg, ˜100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.97 (d, J=6.44 Hz, 3 H) 1.02 (d, J=6.44 Hz, 3 H) 1.54-1.67 (m, 1 H) 1.73-1.91 (m, 2 H) 2.43 (s, 3 H) 4.57-4.65 (m, 1 H) 7.14 (d, J=2.54 Hz, 1 H) 7.28 (dd, J=8.49, 1.27 Hz, 1 H) 7.46-7.58 (m, 4 H) 7.97 (d, 2 H) 8.44 (d, J=2.34 Hz, 1 H), two protons (COOH and NH) were exchanged. LC-MS: m/z 349.1 (M+1). This material will be used for the next step reaction without further work-up.

Provenance & Evidence