Derivatives of indol-2-one for treating neurological disorders, gastrointestinal disorders and cardiovascular disorder
A Derivative, Indole Technology, Applied in 3 Fields
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Embodiment 1
[0096] 5-Chloro-3-ethyl-1,3-dihydro-2H-indol-2-one
[0097] 1.68 g (0.01 mole) of 5-chloro-oxindole was dissolved in 20 mL of ethanol, and 1.0 g of Raney nickel was added to the solution. The reaction mixture was reacted in an autoclave at 110° C. for 36 hours. The catalyst was then filtered off, the solvent was evaporated and the residue was recrystallized from a mixture of hexane and ethyl acetate. Yield: 0.86 g of white powder (44%).
[0098] M.p.: 121-123°C (hexane-ethyl acetate)
[0099] IR (KBr): 3156, 1701 (C=O), 782cm -1 .
[0100] 1 H-NMR (CDCl 3 ): 9.27 (br s, 1H, NH), 7.21 (1H, s, H-4), 7.19 (d, 1H, J=8.8Hz, H-6), 6.85 (d, 1H, J=8.1Hz, H-7), 3.47(t, 1H, J=5.5Hz, H-3), 2.03(m, 2H, CH 2 ), 0.92(t, 3H, J=7.0Hz, CH 3 ) ppm.
[0101] 13 C-NMR (CDCl 3 ): 180.5, 140.4, 131.2, 127.8, 127.6, 124.5, 110.7, 47.5, 23.5, 9.9ppm.
[0102] Formula C 10 h 10 Elemental analysis of ClNO (195.65):
[0103] Calculated: C 61.39, H 5.15, N 7.16, Cl 18.12%.
[0104] Found...
Embodiment 2
[0106] 5-Bromo-3-ethyl-1,3-dihydro-2H-indol-2-one
[0107] 3-Ethyloxindole (16.1 g; 0.10 mole) was dissolved in 350 mL of acetonitrile, the solution was cooled to 0° C., and N-bromosuccinimide (17.8 g; 0.10mole) in 150mL acetonitrile solution. The reaction mixture was stirred at 0°C for 1 hour and then at room temperature for 3 hours. The solution is evaporated and the white substance is isolated in crystalline form, extracted with dichloromethane and 1M NaOH solution, the organic phase is extracted again with basic water in order to remove the succinimide. The organic phase was dried over sodium sulfate, filtered and evaporated. The white material was isolated and recrystallized from a mixture of heptane and ethyl acetate. Yield: 15.24 g of white powder (63%).
[0108] M.p.: 125-127°C (heptane-ethyl acetate)
[0109] IR(KBr): 3154, 1700 (C=O), 812cm -1 .
[0110] 1 H-NMR (CDCl 3 , TMS, 400MHz): 8.90(1H, s), 7.36-7.32(2H, m), 6.81(1H, d, J=8.9Hz), 3.43(1H, t, J=5.8Hz)...
Embodiment 3
[0118] 3-(4-Chlorobutyl)-3-ethyl-1,3-hydro-2H-indol-2-one
[0119] The title compound was prepared following Procedure "A" starting from 3-ethyl-1,3-hydro-2H-indol-2-one and 1-bromo-4-chlorobutane.
[0120] M.p.: 104-105°C (hexane-ethyl acetate).
[0121] IR (KBr): 3181, 2941, 1700, 1306, 755cm -1 .
[0122] 1 H-NMR (CDCl 3 , TMS, 400MHz): 8.57 (br s, 1H, NH), 7.21 (dt, 1H, J=7.6, 1.5Hz, H-6), 7.12 (d, 1H, J=7.4Hz, H-4), 7.06(dt, 1H, J=7.5, 1.0Hz, H-5), 6.92(d, 1H, J=7.7Hz, H-7), 3.39(t, 2H, J=6.7Hz, CH 2 Cl), 1.96-1.84 (m, 2H, CH 2 ), 1.83-1.74 (m, 2H, CH 2 ), 1.74-1.60 (m, 2H, CH 2 ), 1.24-1.18(m, 1H), 1.08-1.03(m, 1H), 0.64(t, 3H, J=7.4Hz, CH 3 ) ppm.
[0123] 13 C-NMR (CDCl 3 , TMS, 101MHz): 182.4, 141.2, 132.3, 127.7, 123, 0, 122.5, 109.6, 54.1, 44.4, 36.8, 32.7, 31.0, 21.8, 8.5ppm.
[0124] Formula C 14 h 18 Elemental analysis of ClNO (251.76):
[0125] Calculated: C 66.79, H 7.21, N 5.56, Cl 14.08%.
[0126] Found values: C 66.89, H 7.16, N 5.84, Cl 14....
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