2-Nitrodibenzofuran → 2-Dibenzofuranamine

HRID 1750903Notes

Reaction equation

HRID 1750903 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1)([O-])=O.[H][H]>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 887292-NitrodibenzofuranHCID 178418361HCID 178418361, compound

Product 1

HCID 194052-DibenzofuranamineYield 134.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

In a Parr hydrogenation bottle, 10% Pd/C (0.77 g, 0.724 mmol) was added and the bottle purged with nitrogen. Next 2-nitrodibenzo[b,d]furan (15 g, 44.3 mmol) in 180 mL of ethyl acetate was added and the mixture was hydrogenated on a Parr Hydrogenator until no more hydrogen is taken up by the solution. The catalyst was filtered off through Celite and washed with ethyl acetate. The filtrate was evaporated and pre-absorbed onto Celite. The Celite mixture was purified using a Varian 400 g column eluting with dichloromethane. 10.9 g of product was obtained.

Workup

  1. customthe bottle purged with nitrogen
  2. filtrationThe catalyst was filtered off through Celite
  3. washwashed with ethyl acetate
  4. customThe filtrate was evaporated
  5. custompre-absorbed onto Celite
  6. customThe Celite mixture was purified
  7. washeluting with dichloromethane

Sources & evidence

ORD record
ord-41852189bc49472cb42b88f3cce2779c
Source dataset
uspto-grants-2015_10
Patent number
US09156870B2

Reaction notes

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