Sodium Carbonate → 7-(3-Amino-phenylamino)-1,3-dihydro-indol-2-one

Beteiligte Stoffe

Reaktionsschritte

[2-Amino-3-(3-amino-phenylamino)-phenyl]-acetic acid ethyl ester (0.50 g, 1.7 mmol) is refluxed in 1 N hydrochloric acid for 30 minutes. The reaction mixture is cooled to room temperature and basified with saturated Na2CO3. The mixture is then extracted with ethyl acetate (30 ml×3). The organic layers are combined, dried with Na2SO4 and concentrated. The residue is purified by flash column chromatography (silica gel, eluted with ethyl acetate-methanol with 0.5% NH3) to give the desired compound. 1H NMR (DMSO-d6) δ 4.93 (s, 2H), 6.06 (d, 1H, J=6.8 Hz), 6.14 (d, 1H, J=8.0 Hz), 6.21 (s, 1H), 6.78 (d, 1H, J=7.2 Hz), 6.85 (t, 2H, J=8.0 Hz), 6.97 (s, 1H), 7.05 (d, 1H, J=8.0 Hz), 9.96 (s, 1H); LC-MS: 240.1 (MH+).

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