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A facile synthesis of 7‐chloromethyl‐1 H ‐indole‐2‐carboxylates: Replacement of a sulfonic acid functionality by chlorine
Author(s) -
Pete Béla,
Varga Frigyes,
Kovács János
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420422
Subject(s) - chemistry , thionyl chloride , methanesulfonic acid , aminolysis , indole test , chlorine , organic chemistry , sulfonic acid , chloride , sulfur , catalysis
Valuable new synthetic intermediates, 7‐chloromethyl‐1 H ‐indole‐2‐carboxylates ( 3a‐d ), were prepared by the facile elimination of sulfur dioxide under the influence of thionyl chloride from 2‐ethoxycarbonyl‐1 H ‐indole‐7‐methanesulfonic acids ( 1a‐d ), easily accessible by Fischer‐type indolisation. The 7‐chloromethylindoles easily underwent methanolysis and aminolysis.