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

HRID 1658276Notes

Reaction equation

HRID 1658276 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]>[Ni].C(O)C>[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

5

Reactant 2

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

Product 1

HCID 38411022,3-Dihydro-1-benzofuran-5-amine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 10 g. of 5-nitro-2,3-dihydrobenzofuran, 2.5 g. of Raney Nickel and 50 ml. of ethanol is hydrogenated in a Parr apparatus at a hydrogen pressure of 50 p.s.i. and room temperature until the uptake of hydrogen ceases. The resulting mixture is filtered to remove catalyst and the filtrate evaporated in vacuo to obtain an oil of 2,3-dihydro-5-benzofuranamine.

Workup

  1. additionA mixture of 10 g
  2. customroom temperature
  3. filtrationThe resulting mixture is filtered
  4. customto remove catalyst
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-aef4b54b93764191b4a52cfc107bc5fe
Source dataset
uspto-grants-1976_06
Patent number
US03963717

Reaction notes

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