HCID 70239958, compound → HCID 21191893, compound

HRID 1069600Notes

Reaction equation

HRID 1069600 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][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([CH3:20])=[C:6]2[CH2:21][C:22]([NH:24]N)=[O:23]>C(O)C.[Ni]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:7]([CH3:20])=[C:6]2[CH2:21][C:22]([NH2:24])=[O:23]

Participants

4

Reactant 1

HCID 70239958HCID 70239958, compound

Product 1

HCID 21191893HCID 21191893, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1.27 g (3.68 mmol) of 5-methoxy-2-methyl-1-octyl-1H-indole-3-acetic acid hydrazide and 1 g of Raney Ni in 60 mL of ethanol was heated to maintain reflux for 3 hours, cooled, the solvent poured off the settled catalyst, treated with filter aid and filtered. The filtrate was concentrated to give 1.03 g (85% yield) of 5-methoxy-2-methyl-1-octyl-1H-indole-3-acetamide, mp, 96-98° C.

Workup

  1. temperaturewas heated
  2. temperatureto maintain
  3. temperaturereflux for 3 hours
  4. temperaturecooled
  5. additionthe solvent poured off the settled catalyst
  6. additiontreated
  7. filtrationwith filter aid
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-1e1654b6c546460c9cb471d558913d22
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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