4-Methylphenylhydrazine monohydrochloride → Ethyl 5-Methyl-2-phenyl-1H-indole-3-butanoate

HRID 395589Notes

Reaction equation

HRID 395589 reaction equation
O=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].Cl.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26]N)=[CH:22][CH:21]=1>>[CH3:19][C:20]1[CH:21]=[C:22]2[C:23](=[CH:24][CH:25]=1)[NH:26][C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[C:3]2[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

3

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 3681727Ethyl 6-oxo-6-phenylhexanoate

Product 1

HCID 18175131Ethyl 5-Methyl-2-phenyl-1H-indole-3-butanoateYield 58%

Procedure

The expected ester is obtained in the form of a brown solid with a yield of 58% by following a procedure analogous to Preparation X and starting from ethyl ε-oxobenzenehexanoate and 4-methylphenylhydrazine hydrochloride.

Workup

  1. customanalogous to Preparation X

Sources & evidence

ORD record
ord-5a414143a9f946b48bfcd6a1f0524824
Source dataset
uspto-grants-2003_08
Patent number
US06605633B1

Reaction notes

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