Ethanol → 5-Methyl-2,3-dihydro-1-benzofuran-7-amine

HRID 1474525Notes

Reaction equation

HRID 1474525 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.C(O)C>ClCCl.[C].[Pd]>[CH3:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5]2[O:9][CH2:8][CH2:7][C:6]=2[CH:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 552848275-Methylbenzofuran-7-amine

Product 1

HCID 552848285-Methyl-2,3-dihydro-1-benzofuran-7-amineYield 87.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

5-Methylbenzofuran-7-ylamine (1.3 g, 8.8 mmol) and 10% palladium carbon (500 mg) were added to ethanol (50 ml), followed by conduction of catalytic reduction at room temperature under ordinary pressure. The catalyst was removed by celite filtration, and the obtained filtrate was condensed under reduced pressure. The residue was dissolved in dichloromethane, dried over anhydrous magnesium sulfate, and then concentrated to dryness under reduced pressure, giving a white powder of 5-methyl-2,3-dihydrobenzofuran-7-ylamine (1.15 g, yield: 87%).

Workup

  1. customfollowed by conduction of catalytic reduction at room temperature under ordinary pressure
  2. customThe catalyst was removed by celite filtration
  3. customcondensed under reduced pressure
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-f53b8641045c4f2dbd2b849205adb762
Source dataset
uspto-grants-2015_04
Patent number
US09018229B2

Reaction notes

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