HCID 54360168, compound → HCID 54054916, compound

HRID 266702Notes

Reaction equation

HRID 266702 reaction equation
[C:1]1([NH:7][C:8](=[O:25])[C:9]([C:23]#[N:24])=[CH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H][H]>C(O)C.[Pd]>[C:1]1([NH:7][C:8](=[O:25])[C:9]([C:23]#[N:24])=[CH:10][C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH2:20])[CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 54360168HCID 54360168, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 54054916HCID 54054916, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-phenyl β-(5-nitro-3-indolyl)-α-cyanoacrylamide (3.324 g, 0.010 mol) in anhydrous ethanol (200 ml) was added palladium on charcoal (0.200 g) and the mixture was hydrogenated at room temperature and atmospheric pressure until 3 equivalent of hydrogen has been taken up. The hydrogen uptake was graphed as function of time. The catalyst was filtered and the solution concentrated under vacuum until crystallization began. The mixture was cooled to 0°-5° C., filtered, the residue washed with ice-cooled ethanol and dried under vacuum. Thus almost pure title compound was obtained in about 80% yield (2.416 g). An analytical pure sample was obtained by crystallization from ethanol.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe catalyst was filtered
  3. concentrationthe solution concentrated under vacuum until crystallization
  4. temperatureThe mixture was cooled to 0°-5° C.
  5. filtrationfiltered
  6. washthe residue washed with ice-
  7. temperaturecooled ethanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-02d12dbcbcec41e097b3ba45ac38571e
Source dataset
uspto-grants-1997_07
Patent number
US05652250

Reaction notes

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