Hydrochloric Acid → HCID 67282261, compound

Temperature

95 °C

To a solution of 3-hydroxy-1-methylpyridin-4(1H)-one hydrochloride (100.0 g, 0.62 mol) dissolved in a solution of 6N NaOH (206.9 mL) at ice-water bath was added trifluoroacetaldehyde methyl hemiacetal (131.9 mL, 1.24 mmol). The resulting solution was heated to 95° C. for overnight. The reaction mixture was then cooled, and at ice-water bath the pH of the mixture was adjusted to about 5 using a 6N HCl solution. The precipitated solid was collected by filtration, and the solid was thoroughly washed with de-ionized water (100 mL×2), and then dried under vacuum at 43° C. for overnight to afford 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (94.8 g) as a white solid. Yield=68% yield; 1H NMR (90 MHz, MeOD-D4) δ (ppm): 7.60 (d, J=7.1 Hz, 1H), 6.40 (d, J=7.2 Hz, 1H), 5.92 (q, J=8.2 Hz, 1H), 3.98 (s, 3H); MS m/z 224 [M+1], 158 (100%).

1. temperatureThe reaction mixture was then cooled
2. customat ice-water bath the pH of the mixture was adjusted to about 5
3. filtrationThe precipitated solid was collected by filtration
4. washthe solid was thoroughly washed with de-ionized water (100 mL×2)
5. customdried under vacuum at 43° C. for overnight

ORD record

ord-fcfbbe9669f1406c8e47b22fde6dffff

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073865B2