Reaction #552203

ord-d11b2d305be64229a697beedc72a21a3

Reaction equation

Cc1ccc([N+](=O)[O-])c2c1CC(C)O2
1C
Cc1ccc([N+](=O)[O-])c2c1CC(C)O2
2,3-dihydro-2,4-dimethyl-7-nitrobenzofuran
[H][H]
hydrogen
→
Cc1ccc(N)c2c1CC(C)O2
7-amino-2,3-dihydro-2,4-dimethylbenzofuran

Reactants

Cc1ccc([N+](=O)[O-])c2c1CC(C)O2
1C
Cc1ccc([N+](=O)[O-])c2c1CC(C)O2
2,3-dihydro-2,4-dimethyl-7-nitrobenzofuran
[H][H]
hydrogen

Reagents

[Ni]
Raney nickel

Solvents

C1CCOC1
tetrahydrofuran

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationfiltered
  2. 2
    OtherThe solvent was evaporated from the filtrate

Procedure

A mixture of 24.3 g of 1C, 200 ml of tetrahydrofuran (THF) and 2 g of activated Raney nickel catalyst was treated with hydrogen (40 psig) in a Parr shaker three hours, then filtered. The solvent was evaporated from the filtrate to give 7-amino-2,3-dihydro-2,4-dimethylbenzofuran (1D), as an amber syrup.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04550121uspto-grants-1985_10