Water → 2,7,9-Trimethyl 4,5-dihydro-4,5-dioxo-1H-pyrrolo(2,3-f)quinoline-2,7,9-tricarboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a suspension of 5-methoxy-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester (about 250 g, 0.67 mol) in acetonitrile (ACN) (about 7.5 L), a solution of ceric ammonium nitrate (about 1.83 kg, 3.35 mol) in about 2.25 L of water is added over a period of about 30 minutes at about −5° C. The reaction mixture is stirred at about −5° C. over a period of about 1.5 hours. Thereafter, resulting reaction mass is filtered, washed with water and dried to obtain the product [4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid trimethyl ester] as a bright orange solid (about 145 g, 58%). 1H NMR (DMSO-d6, 300 MHz): 3.90 (s, 3H), 3.97 (s, 3H), 4.05 (s, 3H), 7.29 (d, J=1.8 Hz, 1H), 8.56 (s, 1H), 12.52 (s, 1H); LC-MS (ESI): 373.0 (M-H).

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