HCID 10852391, compound → HCID 10732550, compound

HRID 1069552Notes

Reaction equation

HRID 1069552 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[C:6]2[CH2:19][C:20]([NH:22]N)=[O:21]>[Ni].CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[C:6]2[CH2:19][C:20]([NH2:22])=[O:21]

Participants

4

Reactant 1

HCID 10852391HCID 10852391, compound

Product 1

HCID 10732550HCID 10732550, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

One gram of Raney nickel was added to 790 mg (2.4 mmol) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetic acid hydrazide in 120 mL of EtOH and the mixture heated at reflux for 2 hours. After filtering off the catalyst, the filtrate was concentrated at reduced pressure and the residue triturated with ether to give 675 mg (89% yield) of 5-methoxy-1-(phenylmethyl)-1H-indole-3-acetamide, mp, 156-158° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 2 hours
  3. filtrationAfter filtering off the catalyst
  4. concentrationthe filtrate was concentrated at reduced pressure
  5. customthe residue triturated with ether

Sources & evidence

ORD record
ord-a14f1e119cf24c02bc280998439b2042
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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