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

HRID 1769361Notes

Reaction equation

HRID 1769361 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-dimethylpropanoateYield 39.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture containing 4-methoxyphenyl hydrazine HCl (70.66 g, 0.405 mol) and methyl 5-(t-butylthio)-2,2-dimethyl-4-oxopentanoate (99.54 g, 0.405 mol) in tBuOH (400 ml) was heated at a gentle reflux for 48 hours. The mixture was allowed to cool to RT and the precipitated NH4Cl was removed by filtration. The residue was concentrated and fractionated on a plug of silica using EtOAc/hexane (1:3) as eluent. Evaporation of the appropriate fraction gave an orange-brown solid which was crystallized from EtOH (100 ml). Yield from two crops afforded 55.6g of the title compound.

Workup

  1. temperaturewas heated at
  2. temperaturea gentle reflux for 48 hours
  3. customthe precipitated NH4Cl was removed by filtration
  4. concentrationThe residue was concentrated
  5. customEvaporation of the appropriate fraction
  6. customgave an orange-brown solid which
  7. customwas crystallized from EtOH (100 ml)
  8. customYield from two crops

Sources & evidence

ORD record
ord-12b1db2e6fbb416190807627b5895735
Source dataset
uspto-grants-1995_01
Patent number
US05380850

Reaction notes

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