1-Nitrodibenzofuran → 1-Dibenzofuranamine

HRID 1750909Notes

Reaction equation

HRID 1750909 reaction equation
[N+:1]([C:4]1[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>[Pd].C(OC(=O)C)C>[C:4]1([NH2:1])[C:12]2[C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[O:9][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 1507531-Nitrodibenzofuran

Product 1

HCID 6030991-DibenzofuranamineYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-nitrodibenzo[b,d]furan (7.3 g, 34.2 mmol) and 730 mg 10% Pd/C were added to 150 mL ethylacetate and the reaction mixture was hydrogenated at 50 psi. Reaction mixture was then filtered out and concentrated under vacuum. Crude product was purified by flash chromatography over silica gel with 90% DCM/Hexanes. Target compound (5.1 g, 82% yield) was isolated as off white solid.

Workup

  1. customReaction mixture
  2. filtrationwas then filtered out and
  3. concentrationconcentrated under vacuum
  4. customCrude product was purified by flash chromatography over silica gel with 90% DCM/Hexanes

Sources & evidence

ORD record
ord-3f238a6419364aae8306b951be27b049
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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