Ammonium Hydroxide → 1-(2H-1,3-Benzodioxol-5-yl)ethan-1-amine

HRID 2307404Notes

Reaction equation

HRID 2307404 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1.[OH-].[NH4+:14]>[Ni].CO>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([NH2:14])[CH3:11])=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 76622Acetopiperone

Product 1

HCID 1294981-(2H-1,3-Benzodioxol-5-yl)ethan-1-amineYield 45%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

A suspension of Raney nickel (1 mL) in methanol (5 mL) and ammonium hydroxide (1 mL) was added to a solution of 1-(1,3-benzodioxol-5-yl)acetaldehyde, oxime (Preparation 1, 8.98 g, 50 mmole) in methanol (50 mL). The reaction mixture was hydrogenated (shaken on a Parr hydrogenator under H2 atmosphere at 60 psi) for 24 hours. The reaction mixture was filtered, and the resultant filtrate was concentrated in vacuo to provide the title compound as an oil (3.68 g, 45%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe resultant filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-baeb9a8fb70e4a0d90a82a6510d77643
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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