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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

2-Hydroxyindole Compounds. Alkylation of 3-Acetyl-1-benzyl-2-hydroxy-5-,ethoxyindole Under Basic Conditions

HM Hugel, RJ Greenwood and MF Mackay

Australian Journal of Chemistry 45(12) 1953 - 1959
Published: 1992

Abstract

Alkylation of 3-acetyl-1-benzyl-2-hydroxy-5-methoxyindole with benzyl bromide in the presence of base resulted in isolation of the C- alkylated product which has been shown by X-ray crystallographic analysis to be 3-acetyl-1,3-dibenzyl-5-methoxy-1,3-dihydro-2H-indol-2-one (5c) in accord with the spectroscopic data. Triclinic crystals of (5c) belong to the space group P1 with a 10.649(3), b 13.736(3), c 14.555(2) Ǻ, α: 86-73(2), β 85.98(2), γ 78-01(2)° and Z 4. Least-squares refinement with 1996 observed data converged at R 0.061. Molecular mechanics was used to calculate the minimum-energy structure of (5c) which is compared with the X-ray results.

https://doi.org/10.1071/CH9921953

© CSIRO 1992

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