2'-Methoxy-3-nitrobiphenyl-4-acetic acid → 6-(2-Methoxyphenyl)-1,3-dihydroindol-2-one

Participants

Reaction Conditions

Reaction Steps

Iron chips (5 g) were added in one portion to 9.8 g of 2′-methoxy-3-nitrobiphenyl-4-acetic acid in 50 mL of glacial acetic acid and heated to 100° C. for 3 hours. 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, water, brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel in ethyl acetate:hexane 1:2 to give 5.4 g (69% yield based on 5-bromo-2-fluoronitrobenzene) of 6-(2-methoxyphenyl)-2-oxindole as a rose colored solid.

Provenance & Evidence