Ammonium Hydroxide → 1-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-amine

HRID 2307405Notes

Reaction equation

HRID 2307405 reaction equation
[C:1]([C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][CH2:10][C:6]=2[CH:5]=1)(=O)[CH3:2].[OH-].[NH4+:14]>CO.[Ni]>[O:8]1[C:7]2[CH:11]=[CH:12][C:4]([CH:1]([NH2:14])[CH3:2])=[CH:5][C:6]=2[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 1452201-(2,3-Dihydro-5-benzofuranyl)ethanone

Product 1

HCID 167684331-(2,3-Dihydro-1-benzofuran-5-yl)ethan-1-amineYield 70%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-acetyl-2,3-dihydrobenzo[b]furan, oxime, (Preparation 3, 2.7 g, 16 mmole) in methanol (50 mL), ammonium hydroxide (5 mL) and Raney nickel (3 mL) was hydrogenated on a Parr hydrogenator (H2, 50 psi) for 2 days. The reaction mixture was filtered through Celite and the resultant filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using methanol (100%) to give the title compound (1.74 g, 70%) as a brown oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe resultant filtrate was concentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-d5e14bbb7ac344b896c0e9d31f4a611b
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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