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Stage #1: With sodium hydrogencarbonate; potassium hexacyanoferrate(III) In water for 0.0833333 h; Stage #2: With sodium hydroxide In water for 0.25 h;
To a solution of L-DOPA (1) (500 mg, 2.5 mmol) inH2O (250 mL) was added a solution of K3[Fe(CN)6] (6.48 g, 19.7 mmol) in 0.5 M NaHCO3 aq (30 mL),and the solution was stirred for 5 min. NaOH (35 mL. 1 M) was added, and the solution was stirredfor 15 min. HCl (10 mL, 6 M) was then added to the reaction mixture to adjust the value of pHto 1. The reaction mixture was extracted with EtOAc (3 125 mL). The organic layer was washedwith brine containing Na2S2O5 (0.095 g) and brine, dried over MgSO4, filtrated, and concentrated.The residue was suspended in n-hexane. After the insoluble material was removed by filtration,the supernatant was evaporated to afford 5,6-dihydroxy-2-indolylcarboxylic acid (9) (350.4 mg, 72percent)as a colorless, amorphous solid. 1H-NMR (270 MHz, acetone-d6)δ ppm: 10.37 (s, 1H), 7.05 (s, 1H), 7.00(s, 1H), 6.98 (s, 1H); 13C-NMR (68 MHz, acetone-d6) δ ppm: 163.0, 146.9, 142.6, 134.0, 126.8, 112.7, 108.7,105.8, 97.6; HRMS (ESI) m/z [M + H]+ calcd. C9H8NO4 194.0448, found 194.0447; UV (CH3OH): max(") = 320 (22400)
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