HCID 70665405, compound → HCID 68205826, compound

HRID 333543Notes

Reaction equation

HRID 333543 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([NH:14][C:15]2[C:20]([N+:21]([O-])=O)=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][CH:2]=1>[Pd].C(O)C>[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4]([NH:14][C:15]2[C:20]([NH2:21])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 70665405HCID 70665405, compound

Product 1

HCID 68205826HCID 68205826, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% palladium on carbon (10%; 0.50 g, 0.47 mmol) was added to a Parr hydrogenation bottle. The bottle was purged with nitrogen. Next, N-(dibenzo[b,d]furan-4-yl)-3-nitropyridin-2-amine (3.8 g, 12.45 mmol) and 200 mL ethanol were added. The reaction mixture was hydrogenated overnight using a Parr hydrogenator. The reaction mixture was filtered through Celite® and the Celite® washed with dichloromethane and ethyl acetate. The filtrate was evaporated leaving a dark brown solid, which was not purified (3.32 g, 97%).

Workup

  1. customThe bottle was purged with nitrogen
  2. filtrationThe reaction mixture was filtered through Celite®
  3. washthe Celite® washed with dichloromethane and ethyl acetate
  4. customThe filtrate was evaporated
  5. customleaving a dark brown solid, which
  6. customwas not purified (3.32 g, 97%)

Sources & evidence

ORD record
ord-31d2ed1aa0c046e48320c28693dbd273
Source dataset
uspto-grants-2014_11
Patent number
US08883322B2

Reaction notes

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