72041-25-9

Upstream product

• 3920-67-0 2-methyl-2-phenyl-1,2-dihydro-3H-indol-3-one 
• 57309-27-0 2-methyl-2-phenyl-3-oxoindolin-1-yloxyl 

Relevant academic research and scientific papers

Reactions of 1,2-dihydro-2-methyl-2-phenyl-3H-indole-3-one with various halogenating reagents

1,2-Dihydro-2-methyl-2-phenyl-3H-indole-3-one (indoxyl) undergoes halogenation with N-chloro- and N-bromosuccinimide and N-chlorobenzotriazole forming 5- and/or 7-halogenated indoxyls. Initial one-electron transfer could be ruled out, and the reaction seems to occur either by an electrophilic aromatic substitution process or by the intermediate formation of N-haloindoxyl, which rearranges via a nitrenium ion to the reaction products. In experiments with I2/AgClO4, FeCl3, Ar3NSbCl6/Bu4NCl, where the radical cation is really formed, 5,5′-dimers and halogenated dimers were always obtained together with halogenated monomers. In the reaction with CuCl2 only the 5-substituted monomer was obtained. Acta Chemica Scandinavica 1998.

ACID TREATMENT OF 2-METHYL-2-PHENYL-3-OXO-INDOLIN-1-OXYL

2-Methyl-3-oxo-indolin-1-oxyl 10 with trifluoroacetic acid gives the disproportionation products 11 and 12.With dry HCl or HBr it undergoes halogenation and deoxygenation and yield halogenated indoxyls 13a-c and 14a-c, and with HI it undergoes deoxygenation to indoxyl 11 or reduction to hydroxylamine 15, depending on the reaction solvent.A deoxygenation mechanism is proposed on the basis of experimental evidence.