5-Nitro-2,3-dihydro-1-benzofuran → 2,3-Dihydro-1-benzofuran-5-amine

HRID 1988171Notes

Reaction equation

HRID 1988171 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:11][CH2:10][CH2:9][C:8]=2[CH:12]=1)([O-])=O.[H][H]>CO.ClCCl.[Pd]>[O:11]1[C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:12][C:8]=2[CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 218165855-Nitro-2,3-dihydro-1-benzofuranHCID 178418361HCID 178418361, compound2×

Product 1

HCID 38411022,3-Dihydro-1-benzofuran-5-amineYield 97.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a suspension of 10.3 g (62.37 mmol) of 5-nitro-2,3-dihydrobenzofuran in 50 mL of MeOH and 10 mL of dichloromethane was added 350 mg of 10% palladium on carbon and the mixture was placed under 55 psi of hydrogen gas. Hydrogen gas uptake was evident during the first 30 minutes. After 18 hours, the mixture was then filtered through diatomaceous earth and concentrated to afford 8.2 g of 2,3-dihydrobenzofuran-5-ylamine as a gray solid which was used without further purification.

Workup

  1. customwas evident during the first 30 minutes
  2. filtrationthe mixture was then filtered through diatomaceous earth
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-914f94813c5a4dcfa1f29dac697c7f00
Source dataset
uspto-grants-2009_06
Patent number
US07553966B2

Reaction notes

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