HCID 86670500, compound → 4-Dibenzofuranamine

HRID 333541Notes

Reaction equation

HRID 333541 reaction equation
[N:1]([C:4]1[C:9]2[O:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:8]=2[CH:7]=[CH:6][CH:5]=1)=[N+]=[N-]>[OH-].[Pd+2].[OH-].C(O)C>[CH:7]1[C:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[O:10][C:9]=2[C:4]([NH2:1])=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 86670500HCID 86670500, compound

Product 1

HCID 4593514-Dibenzofuranamine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

Palladium hydroxide (20%, 0.75 g, 1.068 mmol) was added to a Parr hydrogenation bottle, and the bottle was purged with nitrogen. Next, 4-azidodibenzo[b,d]furan (7.39 g, 35.3 mmol) and 150 mL ethanol were added, and the reaction mixture was hydrogenated on Parr hydrogenator overnight. The reaction mixture was filtered through a pad of Celite®, and the Celite® was washed with dichloromethane. The filtrate was evaporated, and the residue was purified by column chromatography eluting with 50% dichloromethane/hexanes (5.58 g, 86%).

Workup

  1. customthe bottle was purged with nitrogen
  2. customwas hydrogenated on Parr hydrogenator overnight
  3. filtrationThe reaction mixture was filtered through a pad of Celite®
  4. washthe Celite® was washed with dichloromethane
  5. customThe filtrate was evaporated
  6. customthe residue was purified by column chromatography
  7. washeluting with 50% dichloromethane/hexanes (5.58 g, 86%)

Sources & evidence

ORD record
ord-2ca76a5361c24392b9acaaee6eeb22fd
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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