3-Hydroxy-2-pyridinemethanol hydrochloride synthesis

Yield: 1.57 g

Reaction Conditions:

with hydrogenchloride in acetone

Steps:

3-Hydroxy-2-(hydroxymethyl)pyridine hydrochloride (2)
A mixture of 3-(hydroxymethyl)pyridine (3.00 g, 31.5 mmol), sodium hydroxide (1.26 g, 31.5 mmol), and 37% aqueous solution of formaldehyde (3.00 g, 37.0 mmol) in water (15 mL) was heated for 3 h at 90 °C. Then, the reaction mixture was cooled to ~20 °C and neutralized by the addition of glacial acetic acid. A solution obtained was dried in vacuo. The dry residue was extracted with boiling acetone (200 mL), the insoluble part was filtered off, whereas gaseous hydrogen chloride was passed through the filtrate. A precipitate formed was filtered off. The yield was 1.57 g (31%), a white crystalline compound, m.p. 212- 216 °C (cf. Ref. 33: m.p. 213-216 °C). 1H NMR (DMSO-d6), d: 4.77 (s, 2 H, CH2OH); 6.45 (br.s, 1 H, CH2OH); 7.75 (dd, 1 H, 5-PyH, J1= 8.4 Hz, J2= 5.4 Hz); 8.12 (d, 1 H, 4-PyH, J = 8.4 Hz); 8.20 (d, 1 H, 6-PyH, J = 5.4 Hz); 12.36 (br.s, 1 H, OH). 13C NMR (DMSO-d6), d: 56.22 (s, CH2O); 125.84 (s, CPyr); 129.37 (s, CPyr); 131.16 (s, CPyr); 144.72 (s, CPyr); 153.22 (s, CPyr).

References:

Shtyrlin;Vafina;Pugachev;Khaziev;Nikitina;Zeldi;Iksanova;Shtyrlin, Yu. G. [Russian Chemical Bulletin,2016,vol. 65,# 2,p. 537 - 545][Izv. Akad. Nauk, Ser. Khim.,2016,# 2,p. 537 - 545,9]