2-HYDROXYINDOLE COMPOUNDS - ALKYLATION OF 3-ACETYL-1-BENZYL-2-HYDROXY-5-METHOXYINDOLE UNDER BASIC CONDITIONS

Alkylation of 3-acetyl-l-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-indole-2-one (5c) in accord with the spectroscopic data. Triclinic crystals of (5c) belong to the space group P1BAR with a 10.649(3), b 13.736(3), c 14.555(2) angstrom, alpha 86.73(2), beta 85.98(2), gamma 78.01(2)-degrees 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.