4'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(4-Methoxy-phenyl)-1,3-dihydro-indol-2-one

Participants

Reaction Conditions

Reaction Steps

Iron chips (3.6 g) were added in one portion to 7.2 g 4′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL glacial acetic acid and heated at 100° C. overnight. The reaction mixture was concentrated to dryness, sonicated in ethyl acetate and filtered to remove the insolubles. The filtrate was washed twice with 1 N hydrochloric acid, then with brine, dried over anhydrous sodium sulfate and concentrated to give 2.7 g (54% yield based on 5-bromo-2-fluoronitrobenzene) of 6-(4-methoxyphenyl)-2-oxindole as a rose colored solid.

Provenance & Evidence