4-Methoxyphenylhydrazine hydrochloride → Methyl 3-{5-methoxy-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoate

HRID 1590103Notes

Reaction equation

HRID 1590103 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1.[C:12]([S:16][CH2:17][C:18](=O)[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]>CC(O)(C)C>[C:12]([S:16][C:17]1[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([O:3][CH3:2])[CH:9]=2)[NH:10][C:18]=1[CH2:19][C:20]([CH3:26])([CH3:25])[C:21]([O:23][CH3:24])=[O:22])([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 14980531Methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate

Product 1

HCID 14980549Methyl 3-{5-methoxy-3-[(2-methyl-2-propanyl)sulfanyl]-1H-indol-2-yl}-2,2-dimethylpropanoate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A solution of 22.7 g 1-(4-methoxyphenyl)hydrazine hydrochloride and 24.6 g methyl 5-t-butylthio-2,2-dimethyl-4-oxopentanoate in 500 mL of t-BuOH was heated at reflux under nitrogen for 24 hours. The solvent was removed under reduced pressure and the residue stirred in 900 mL ether. Filtration and evaporation of the Et2O provided an oil which was chromatographed (silica gel; 3% EtOAc in toluene) to provide the title compound as an oil.

Workup

  1. temperatureat reflux under nitrogen for 24 hours
  2. customThe solvent was removed under reduced pressure
  3. filtrationFiltration and evaporation of the Et2O
  4. customprovided an oil which
  5. customwas chromatographed (silica gel; 3% EtOAc in toluene)

Sources & evidence

ORD record
ord-24fd8d811c804280a8d9bfb8bb582339
Source dataset
uspto-grants-1993_04
Patent number
US05202321

Reaction notes

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