Water → (4-Aminophenyl)(5-methylpyridin-2-yl)methanol

A solution of 2-(4-fluorobenzoyl)-5-methylpyridine (3.0 g) and sodium azide (4.97 g) in DMSO (60 ml) was stirred for 24 hours at 90° C. To the reaction mixture was added water, and the mixture was extracted with diethylether. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated under reduced pressure, and a solution of the residue (3.39 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (1.06 g) in THF (40 ml) at 0° C. The mixture was stirred at room temperature for 1 hour, and water (1.06 ml), 15% aqueous solution of sodium hydroxide (1.06 ml) and water (3.18 ml) were sequentially and slowly added dropwise to the solution at 0° C. The mixture was stirred for 64 hours at room temperature, magnesium sulfate was added to the mixture, and the precipitates were removed by filtration (Celite). The reaction mixture was concentrated under reduced pressure, and the residue was recrystallized, to give (4-aminophenyl)(5-methylpyridin-2-yl)methanol (2.07 g) as pale yellow crystals.

1. extractionthe mixture was extracted with diethylether
2. washThe organic layer was washed with water and saturated brine
3. dry with materialdried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. additiona solution of the residue (3.39 g) in THF (40 ml) was added dropwise to a suspension of aluminum lithium hydride (1.06 g) in THF (40 ml) at 0° C
6. additionslowly added dropwise to the solution at 0° C
7. stirringThe mixture was stirred for 64 hours at room temperature
8. additionmagnesium sulfate was added to the mixture
9. customthe precipitates were removed by filtration (Celite)
10. concentrationThe reaction mixture was concentrated under reduced pressure
11. customthe residue was recrystallized

ORD record

ord-13d5321860ba4e4c89cdbba0c692f323

Source dataset

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07262185B2