Water → 1-(2H-1,3-Benzodioxol-2-yl)methanamine

HRID 660406Notes

Reaction equation

HRID 660406 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH:2]1[C:10]([NH2:12])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH:2]1[CH2:10][NH2:12]

Participants

5

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.

Workup

  1. customto destroy the excess LAH
  2. additionAqueous sodium hydroxide (3.0 M, 100 mL) was added
  3. extractionthe solution was extracted with ethyl acetate (3×100 mL)
  4. washThe combined organic solution was washed with water
  5. dry with materialdried over MgSO4
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-cd04e336e8b54f1d8662de29ce7d54c8
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

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