2-Iodoaniline → HCID 21753017, compound

Participants

Reaction Steps

A solution of 2.4 g (6 mmol) of 4,5-bis(trimethylsilyloxy)cyclohexa-1,4-diene-1,2-dicarboxylic acid dimethyl ester (Example 1a) and 5.3 g (24 mmol) of 2-iodoaniline in 24 ml of glacial acetic acid is boiled under reflux for 2 hours. The reaction mixture is cooled, the solvent is evaporated off and the dark-brown residue is dissolved in dichloromethane and the solution is washed in succession with 20 ml of 1N HCl, 50 ml of saturated NaHCO3 and twice with 20 ml of water, dried with sodium sulfate and concentrated by evaporation. The residue obtained after concentration by evaporation is chromatographed on silica gel with ethyl acetate/hexane 2:1 and the product fractions are concentrated by evaporation, yielding the title compound in the form of a yellow foam: 1H-NMR (DMSO-d6): δ=7.91 (dxd, J1 =8, J2 =1, 2H), 7.39 (dxdxd, J1 =10, J2 =8, J3 =1, 2H), 7.32 (br s, 2H), 7.22-7.05 (m, 2H), 7.01 (s, 2H), 6.88 (txd, Jt =8, Jd =1, 2H), 3.73 (s, 6H).

Provenance & Evidence