Reaction #2320150

Reaction equation

Lithium aluminum hydride

2-ethylbenzonitrile

water

sodium hydroxide

water

→

title compound

2-ethylbenzylamine

Solvents

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Otherrecooled to 0° C.
2. 2
   workup.STIRRINGto facilitate stirring
3. 3
   FiltrationThe reaction mixture was filtered through celite
4. 4
   Washthe filter cake was washed with tetrahydrofuran (150 mL)
5. 5
   Concentrationthe filtrate was concentrated under reduced pressure
6. 6
   Otherthe residue was partitioned between methylene chloride/saturated sodium chloride
7. 7
   DryingThe organic phase was dried (potassium carbonate)
8. 8
   Filtrationfiltered
9. 9
   Concentrationthe filtrate was concentrated under reduced pressure

Procedure

Lithium aluminum hydride (7.4 g 196 mmol) in tetrahydrofuran (130 mL) was slowly treated with 2-ethylbenzonitrile (4.99 g 38 mmol) in tetrahydrofuran (40 mL) at 0° C. under nitrogen. The mixture was stirred for 30 minutes at 0° C., 2 hours at room temperature, recooled to 0° C., and then slowly treated in succession with water (7.4 mL), 15% sodium hydroxide (7.4 mL) and water (22 mL). Additional tetrahydrofuran (50 mL) was added to facilitate stirring. The reaction mixture was filtered through celite, the filter cake was washed with tetrahydrofuran (150 mL), the filtrate was concentrated under reduced pressure, and the residue was partitioned between methylene chloride/saturated sodium chloride. The organic phase was dried (potassium carbonate), filtered, and the filtrate was concentrated under reduced pressure to provide the title compound. 1H NMR (CDCl3) δ 1.24 (t, 3H), 2.69 (q, 2H), 3.89 (s, 2H), 7.20 (m, 3H), 7.32 (m, 1H).

Source