3-Nitrodibenzofuran → 3-Dibenzofuranamine

HRID 1750897Notes

Reaction equation

HRID 1750897 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[O:9][C:8]=2[CH:16]=1

Participants

4

Reactant 1

HCID 728973-Nitrodibenzofuran

Product 1

HCID 200613-DibenzofuranamineYield 56%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

3-nitrodibenzofuran (30 g, 141 mmol) was stirred in 500 mL ethyl acetate and 3 g of 10% Pd/C were added to the slurry. Reaction mixture was hydrogenated for 30 minutes at 50 psi H2 pressure. Reaction mixture was filtered through a small Celite pad. Filtrate was concentrated under reduced pressure and performed silica gel column using 9:1 DCM/Hexanes as eluent. Final isolated amount was 14.5 g (56% yield).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. filtrationwas filtered through a small Celite pad
  4. concentrationFiltrate was concentrated under reduced pressure
  5. customFinal isolated amount

Sources & evidence

ORD record
ord-11e1baed26344f1ea432a39f5bd59074
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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