HCID 10738003, compound → HCID 11792628, compound

HRID 1069620Notes

Reaction equation

HRID 1069620 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[CH2:25][CH3:26])[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[CH2:25][CH3:26])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 10738003HCID 10738003, compound

Product 1

HCID 11792628HCID 11792628, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 340 mg (0.92 mmol) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetic acid hydrazide and 200 mg of Raney Ni in 20 mL of ethanol was heated to maintain reflux for 2.5 hours. After cooling the solvent was decanted and the Raney Ni washed twice with methylene chloride. The combined organic solvents were filtered, concentrated at reduced pressure and the residue chromatographed on silica gel eluting with ethyl acetate to give 244 mg (74% yield) of 1-[(3-chlorophenyl)methyl]-2-ethyl-5-methoxy-1H-indole-3-acetamide.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 2.5 hours
  4. temperatureAfter cooling the solvent
  5. customwas decanted
  6. washthe Raney Ni washed twice with methylene chloride
  7. filtrationThe combined organic solvents were filtered
  8. concentrationconcentrated at reduced pressure
  9. customthe residue chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-13916a62966046f3b461d1f8f376ce0c
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…