4-Methylpyridine → 1-(2-Hydroxyethyl)-4-methylpyridin-1-ium bromide

Temperature

50 °C

In a 3-neck, round-bottomed flask flushed with nitrogen, 2-bromo-1-ethanol (40.01 mmol), 4-picoline (43.57 mmol) and absolute ethanol (16 mL) were combined and heated for 3.5 hours at 50° C. under nitrogen with stirring. The reaction was stopped and the contents of the flask were transferred to a one-neck round-bottomed flask. The solvent was removed under vacuum and the residue was washed with diethyl ether (4×100 ml) and any remaining solvent was removed under vacuum. The product was obtained as a viscous orange liquid in a 34% yield. 1H NMR (200 MHz, CDCl3) 8.9 (2H, protons on pyridine ring), 8.0 (2H, protons on pyridine ring), 2.6 (3H, CH3), 4.6 (2H, —CH2O), 3.8 (2H, —NCH2—), 5.2 (1H, —OH); IR (neat, cm−1) 3303 (OH), 1640 (aromatic C═N), 1474 (aromatic C—C).

1. customthe contents of the flask were transferred to a one-neck round-bottomed flask
2. customThe solvent was removed under vacuum
3. washthe residue was washed with diethyl ether (4×100 ml)
4. customany remaining solvent was removed under vacuum
5. customThe product was obtained as a viscous orange liquid in a 34% yield

ORD record

ord-27b3a24721c44cc890298a407c932ada

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06894169B1