Reaction #1106681

Reaction equation

Benzo[1,3]dioxole-2-carboxylic acid amide

Lithium aluminum hydride

water

→

C-benzo[1,3]dioxol-2-yl-methylamine

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherto destroy the excess LAH
2. 2
   workup.ADDITIONAqueous sodium hydroxide (3.0 M, 100 mL) was added
3. 3
   Extractionthe solution was extracted with ethyl acetate (3×100 mL)
4. 4
   WashThe combined organic solution was washed with water
5. 5
   Dryingdried over MgSO4
6. 6
   OtherThe solvent was evaporated

Procedure

Benzo[1,3]dioxole-2-carboxylic acid amide (5.44 g, 32.9 mmol) was dissolved in tetrahydrofuran (THF, 100 mL). Lithium aluminum hydride (LAH, 1M in THF, 39.5 mL, 39.5 mmol) was added slowly to the solution at room temperature. The reaction was stirred at room temperature for 24 hours. Distilled water was added to destroy the excess LAH. Aqueous sodium hydroxide (3.0 M, 100 mL) was added and the solution was extracted with ethyl acetate (3×100 mL). The combined organic solution was washed with water and dried over MgSO4. The solvent was evaporated to yield C-benzo[1,3]dioxol-2-yl-methylamine as a colorless oil.

Source