Water → 3-(Hydroxymethyl)-6-methylpyridin-2(1H)-one

Temperature

-70 °C

2-hydroxy-6-methylpyridine-3-carboxylic acid (2 g, 13 mmol) was dissolved in dry THF (80 ml), and this solution was cooled to −70° C. LiAlH4 (32 ml, 32 mmol) was then added over a period of 20 min. The reaction mixture was warmed to room temperature and then was heated at 70° C. for 1 hour. After cooling down to 0° C., the reaction mixture was added H2O (2 mL), 10% NaOH (4 mL) and finally H2O (2 mL). The reaction mixture was stirred at room temperature for 1 hour. NaSO4 (6 g) was added, the mixture was stirred for a further 30 min., filtered and washed with MeOH. The filtrate was concentrated to dryness to give the desired product as a solid (2 g, 100%). LCMS (ES+) m/z 140 (MH+).

1. temperatureThe reaction mixture was warmed to room temperature
2. temperaturewas heated at 70° C. for 1 hour
3. temperatureAfter cooling down to 0° C.
4. stirringthe mixture was stirred for a further 30 min.
5. filtrationfiltered
6. washwashed with MeOH
7. concentrationThe filtrate was concentrated to dryness

ORD record

ord-6a2bfdf215d042a1a812adeb3e407d67

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071592B2