Hydrochloric Acid → HCID 69227248, compound

Participants

Reaction Conditions

Reaction Steps

{2-Methyl-6-[3-(quinolin-2-ylamino)-propoxymethyl]-phenoxy}-acetonitrile (270 mg, 0.75 mmol) is dissolved in ethanol (6 mL). 10 N NaOH (750 μL, 7.5 mmol) is added, and the contents are heated to 60° C. for 4 hrs. The reaction is cooled to r.t. 2 N HCl (3.75 mL, 7.5 mmol) is added and the pH is adjusted to ˜4-6. The contents are poured into water (150 mL) and extracted with ethyl acetate (3×75 mL). The organic fractions were pooled and washed with brine (3×100 mL), dried over MgSO4, filtered and reduced under vacuum to dryness. The crude material was pure enough to test as is to give the title compound. 1H NMR (300 MHz, CDCl3) δ 11.04 (s (broad), 1H), 7.88 (d, 1H), 7.73 (d, 1H), 7.52-7.47 (m, 2H), 7.26-7.12 (m, 3H), 7.02-6.97 (m, 1H), 6.90 (d, 1H), 4.66 (s, 2H), 4.47 (s, 2H), 3.69 (t, 2H), 3.57-3.53 (m, 2H), 2.33 (s, 3H), 2.05 (quintet, 2H). MS (ESI) 381 (M+H)+.

Provenance & Evidence