HCID 10642107, compound → HCID 10854831, compound

HRID 1069625Notes

Reaction equation

HRID 1069625 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11]([CH2:20][C:21]([NH:23]N)=[O:22])=[C:10]2[CH3:25])[CH:5]=[CH:6][CH:7]=1>C(O)C.[Ni]>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][C:14]([O:18][CH3:19])=[CH:15][CH:16]=3)[C:11]([CH2:20][C:21]([NH2:23])=[O:22])=[C:10]2[CH3:25])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10642107HCID 10642107, compound

Product 1

HCID 10854831HCID 10854831, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 675 mg (1.9 mmol) of 1-[(3-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetic acid hydrazide and 500 mg of Raney Ni in 25 mL of ethanol was heated to maintain reflux for 3.5 hours and cooled to room temperature. The ethanol was decanted and the Raney Ni washed twice with methylene chloride. The combined solvents were filtered, concentrated at reduced pressure and the residue chromatographed on silica gel (eluted with EtOAc) to give 503 mg (77% yield) of 1-[(3-chlorophenyl)methyl]-5-methoxy-2-methyl-1H-indole-3-acetamide, mp, 171-173° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 3.5 hours
  4. customThe ethanol was decanted
  5. washthe Raney Ni washed twice with methylene chloride
  6. filtrationThe combined solvents were filtered
  7. concentrationconcentrated at reduced pressure
  8. customthe residue chromatographed on silica gel (eluted with EtOAc)

Sources & evidence

ORD record
ord-82020771a6674f119ea93c3048ad70f5
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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