Hydrochloric Acid → 4-(Hydroxymethyl)quinoline

Participants

Reaction Conditions

Reaction Steps

A solution of quinoline-4-carbaldehyde (0.50 g, 3.24 mmol) dissolved in methanol (5 mL) was cooled to 0° C. Sodium borohydride (0.11 g, 2.91 mmol) was then added portion-wise. After 1 h of stirring at 0° C., 2M HCl (aq) was added drop-wise until pH-5. The methanol was then evaporated in vacuo and the aqueous phase was neutralized by addition of saturated aqueous NaHCO3. The aqueous solution was extracted with CH2Cl2 (3×) and the combined organic extracts were washed with saturated NaHCO3 (aq) and brine. The organic solution was dried over Na2SO4, filtered, and concentrated in vacuo to yield quinolin-4-ylmethanol as a yellow solid. MS (ES+): 160 [MH+]. 1H NMR (CDCl3, 400 MHz): δ 2.41 (bs, 1H), 5.25 (bs, 2H), 7.55 (ddd, J=4.4, 1.2, 1.2 Hz, 1H), 7.58 (ddd, J=8.4, 7.2, 1.2 Hz, 1H), 7.73 (ddd, J=8.4, 6.8, 1.6 Hz, 1H), 7.97 (ddd, J=8.4, 1.2, 0.4 Hz, 1H), 8.14 (ddd, J=8.0, 1.2, 0.4 Hz, 1H), 8.90 (d, J=4.4 Hz, 1H).

Provenance & Evidence