HCID 10547377, compound → HCID 11792751, compound

HRID 1069563Notes

Reaction equation

HRID 1069563 reaction equation
[CH2:1]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([CH2:22][C:23]([NH:25]N)=[O:24])=[C:12]1[CH3:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]>CCO.[Ni]>[CH2:1]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([O:20][CH3:21])=[CH:17][CH:18]=2)[C:13]([CH2:22][C:23]([NH2:25])=[O:24])=[C:12]1[CH3:27])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 1

HCID 10547377HCID 10547377, compound

Product 1

HCID 11792751HCID 11792751, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Approximately 1.5 g of Raney Ni was added to 1.5 g (4.0 mmol) of 1-decyl-5-methoxy-2-methyl-1H-indole-3-acetic acid hydrazide in 250 mL of EtOH and the mixture heated at reflux for 3 hours. After cooling the mixture was filtered and the filtrate concentrated at reduced pressure. The residue was crystallized from EtOAc/hexane to give 0.987 g (69% yield) of 1-decyl-5-methoxy-2-methyl-1H-indole-3-acetamide, mp, 110-111° C.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the mixture
  4. filtrationwas filtered
  5. concentrationthe filtrate concentrated at reduced pressure
  6. customThe residue was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-095efe7c22644c06b0d588c366e51d15
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

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