Hydrochloric Acid → 4-(Hydroxymethyl)quinoline

Temperature

0 °C

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).

1. customThe methanol was then evaporated in vacuo
2. additionthe aqueous phase was neutralized by addition of saturated aqueous NaHCO3
3. extractionThe aqueous solution was extracted with CH2Cl2 (3×)
4. washthe combined organic extracts were washed with saturated NaHCO3 (aq) and brine
5. dry with materialThe organic solution was dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD record

ord-e65fe31e05ea46c084e06745f7d6da71

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696225B2