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49649113726
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Representative Experimental Procedure: In a typical experiment, PCC (2.5 mmol, 537 mg) was added to a solution of indole (1 mmol, 117 mg) in 1,2-DCE (5 mL, Polyaniline salt catalyst [15 wt% with respect to indole (17 mg, was added and the reaction mixture was stirred at r.t. or at reflux. Completion of the reaction was monitored by TLC. After completion, the reaction mixture was filtered through a Celite® pad and washed with EtOAc (2x5 mL, The combined organic extracts were dried and evaporated under vacuum. The crude product was purified by silica gel column chromatography (n-hexane-EtOAc, 3:1) to furnish isatin 129 mg, 88, A similar procedure was adopted for the preparation of other isatins, 3-hydroxy oxindoles and the authenticity of the products was confirmed from their 1H NMR and mass spectral data
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1H NMR and mass spectral data.
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49649127228
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Spectral Data for New Compounds, 1-Butyl-5-chloroindoline-2,3-dione (Table 2, entry 8, TLC: RfO-S (30% EtOAc-hexanes, orange solid; mp 62-63 °C. IR(KBr, 3089, 2953, 1737, 1606, 1448, 1339, 1185, 1116, 844, 720 cm-1. 1H NMR (200 MHz, CDCl3, δ, 7.49 (m, J, 8.1 Hz, 2 H, 6.80 (d, J, 8.1 Hz, 1 H, 3.70 (t, J, 7.3 Hz, 2 H, 1.67 (quint, J, 7.3 Hz, 2 H, 1.43 (m, J, 7.3 Hz, 2 H, 0.98 (t, J, 7.3 Hz, 3 H, 13C NMR (200 MHz, CDCl3, δ= 182.5, 157.6, 149.4, 137.5, 129.3, 125.1, 118.3, 111.8, 40.07, 29.08, 20.0, 13.5. MS (ESI, m/z, 238 [M, H, HRMS (ESI, m/z [M, H, calcd for C12H 13NClO2: 238.0634; found 238.0630. 1-Methyl-5- nitroindoline-2,3-dione (Table 2, entry 9, TLC: Rf0.3 (50% EtOAc-hexanes, yellowish orange solid; mp 203 °C. IRKBr, 2924, 1743, 161
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2: 261.1603; found: 261.1606.
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