(4-Methoxyphenyl)hydrazine → (5-Methoxy-2-methyl-3-indoleacetoxy)-benzyl acetate

HRID 1659162Notes

Reaction equation

HRID 1659162 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.C(O[CH2:19][C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])(=O)CCC(C)=O>>[C:20]([O:22][CH:23]([O:22][C:20](=[O:21])[CH2:19][C:23]1[C:7]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:8]=2)[NH:9][C:24]=1[CH3:25])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:21])[CH3:19]

Participants

3

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazineHCID 126583762-Oxo-2-(phenylmethoxy)ethyl 4-oxopentanoate

Product 1

HCID 70621341(5-Methoxy-2-methyl-3-indoleacetoxy)-benzyl acetate

Procedure

condensing 4-methoxyphenylhydrazine or its salts with benzyl levulinoyloxyacetate according to Fischer to form (5-methoxy-2-methyl-3-indoleacetoxy)-benzyl acetate, subsequently acylating the alkali salt thereof with p-chlorobenzoyl chloride to form [1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indole-acetoxy]-benzyl acetate and then catalytically dehydrogenating the benzyl group (see reaction scheme A),

Sources & evidence

ORD record
ord-b19030aa7b954764855971572f646c68
Source dataset
uspto-grants-1976_06
Patent number
US03966956

Reaction notes

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