Reaction #1605775

Reaction equation

water

HCl

2-(5-methylpyridin-2-yl)acetonitrile

Borane tetrahydrofuran

→

2-(5-methylpyridin-2-yl)ethanamine

Yield 41.0%

Solvents

THF

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled to room temperature
2. 2
   Temperaturethe reaction mixture was then heated at 70° C. for 2 hrs
3. 3
   TemperatureAfter cooling
4. 4
   Washthe resulting solution was washed with ether
5. 5
   Otherwas basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3
6. 6
   Extractionthen extracted with ether (5×100 mL)
7. 7
   DryingThe organic layer was dried over MgSO4
8. 8
   Filtrationfiltered
9. 9
   Otherevaporated

Procedure

To a solution of 18 g of crude 2-(5-methylpyridin-2-yl)acetonitrile in dry THF (100 mL) was added dropwise Borane-tetrahydrofuran complex (1.0 M in THF, 232 mL, 232.5 mmol, 4 eq) at 0° C. under N2 atmosphere. The reaction mixture was then heated to 60° C. overnight. The reaction was cooled to room temperature, aq.HCl (6 N, 40 mL) was added carefully and the reaction mixture was then heated at 70° C. for 2 hrs. After cooling, water was added and the resulting solution was washed with ether. The aqueous layer was basified with aq. NaOH (10 N) at 0° C. and saturated with K2CO3 then extracted with ether (5×100 mL). The organic layer was dried over MgSO4, filtered and evaporated to give 7.6 g of crude 2-(5-methylpyridin-2-yl)ethanamine. (96% crude yield)

Source