N-苯基吲哚酮

反应条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of commercially available 1-phenyl-1H-indole-2,3-dione (10.10 g, 45.7 mmol) in ethylene glycol (125 mL) is added powdered potassium hydroxide (7.4 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL). The reaction is heated to 160° C. for 1.5 hr after which it is cooled to room temperature, made acidic with conc. hydrochloric acid, diluted with water and the resulting solids are collected by filtration. The solid is washed with water, dissolved in dichloromethane, dried and the solvent removed to give the 1-phenyl-1H-indol-2-one (8.6 g, 90% yield) as a solid. is cooled to room temperature the resulting solids are collected by filtration The solid is washed with water dissolved in dichloromethane dried the solvent removed

反应条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5° C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane. the aqueous layer is separated extracted with chloroform (3×200 mL) The combined organic layer and extracts is dried filtered concentrated The solid residue is crystallized from ethanol

反应条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5° C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane. the aqueous layer is separated extracted with chloroform (3×200 mL) The combined organic layer and extracts is dried filtered concentrated The solid residue is crystallized from ethanol

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound is prepared in accordance with the procedures described in Latrell, Bartmann, Granzier DE 2 707 268 (1978) as follows. A solution of diphenylamine (40 g, 237 mmol) and triethylamine (66.1 mL, 474 mmol) in toluene (65 mL) is added dropwise to a solution of chloroacetyl chloride (20.7 mL, 260 mmol) in toluene (40 mL) while cooling in an ice-water bath. The cold bath is removed and the reaction mixture is heated at 55-65° C. for 3 hr. The cooled reaction mixture is diluted with toluene (100 mL), filtered and the filtrate concentrated to give 2-chloro-N,N-diphenylacetamide (24.4 g, 42% yield) as a light brown solid. NMR (CDCl3) 7.56-7.19 (10H, m), 4.01 (2H, s). while cooling in an ice-water bath The cold bath is removed The cooled reaction mixture filtered the filtrate concentrated

反应条件: temp:67.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-phenyl-1,3-dihydro-indol-2-one (80 g, 382 mmol), sodium hydroxide (16.06 g, 402 mmol) and tetrahydrofuran (113 ml) is heated to reflux (67° C.) for S hours. The solution is diluted with another portion of tetrahydrofuran (169 ml) and cooled to −10° C. A 20% solution of butyllithium in cyclohexane (122.3 g, 382 mmol) is added at this temperature followed by dimethylcarbonate (51.7 g, 573 mmol). Afterwards, the solution is stirred at −10° C. for 2 hours. Concentrated hydrochloric acid (38 ml) and water (125 ml) are added and the organic solvents are distilled off at reduced pressure. After addition of toluene (345 ml) to the suspension, the pH of the water phase is adjusted to 1.5 using hydrochloric acid (34 ml). After phase separation at 75° C., the organic phase is washed with another portion of water (120 ml), concentrated at reduced pressure and allowed to crystallize at 0° C. to yield 81.2 g of pure title compound (75%). is heated cooled to −10° C the organic solvents are distilled off at reduced pressure After addition of toluene (345 ml) to the suspension After phase separation at 75° C. the organic phase is washed with another portion of water (120 ml) concentrated at reduced pressure to crystallize at 0° C.

反应条件: temp:67.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-phenyl-1,3-dihydro-indol-2-one (80 g, 382 mmol), sodium hydroxide (16.06 g, 402 mmol) and tetrahydrofuran (113 ml) is heated to reflux (67° C.) for S hours. The solution is diluted with another portion of tetrahydrofuran (169 ml) and cooled to −10° C. A 20% solution of butyllithium in cyclohexane (122.3 g, 382 mmol) is added at this temperature followed by dimethylcarbonate (51.7 g, 573 mmol). Afterwards, the solution is stirred at −10° C. for 2 hours. Concentrated hydrochloric acid (38 ml) and water (125 ml) are added and the organic solvents are distilled off at reduced pressure. After addition of toluene (345 ml) to the suspension, the pH of the water phase is adjusted to 1.5 using hydrochloric acid (34 ml). After phase separation at 75° C., the organic phase is washed with another portion of water (120 ml), concentrated at reduced pressure and allowed to crystallize at 0° C. to yield 81.2 g of pure title compound (75%). is heated cooled to −10° C the organic solvents are distilled off at reduced pressure After addition of toluene (345 ml) to the suspension After phase separation at 75° C. the organic phase is washed with another portion of water (120 ml) concentrated at reduced pressure to crystallize at 0° C.

反应条件: temp:67.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 1-phenyl-1,3-dihydro-indol-2-one (80 g, 382 mmol), sodium hydroxide (16.06 g, 402 mmol) and tetrahydrofuran (113 ml) is heated to reflux (67° C.) for S hours. The solution is diluted with another portion of tetrahydrofuran (169 ml) and cooled to −10° C. A 20% solution of butyllithium in cyclohexane (122.3 g, 382 mmol) is added at this temperature followed by dimethylcarbonate (51.7 g, 573 mmol). Afterwards, the solution is stirred at −10° C. for 2 hours. Concentrated hydrochloric acid (38 ml) and water (125 ml) are added and the organic solvents are distilled off at reduced pressure. After addition of toluene (345 ml) to the suspension, the pH of the water phase is adjusted to 1.5 using hydrochloric acid (34 ml). After phase separation at 75° C., the organic phase is washed with another portion of water (120 ml), concentrated at reduced pressure and allowed to crystallize at 0° C. to yield 81.2 g of pure title compound (75%). is heated cooled to −10° C the organic solvents are distilled off at reduced pressure After addition of toluene (345 ml) to the suspension After phase separation at 75° C. the organic phase is washed with another portion of water (120 ml) concentrated at reduced pressure to crystallize at 0° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Potassium t-butoxide (1.63 g, 14.5 mmoles) and 5 ml absolute ethanol were heated to 80°. 1-Phenyl-2(1H,3H)-indolone (2.09 g, 10 mmoles) was added, followed by ethyl formate (1.09 ml, 13.5 mmoles). The mixture was heated 5 minutes, cooled to 25°, and the nearly solid mass diluted with 50 ml H2O and crushed ice, acidified to pH 3 with 3N HCl and title product recovered by filtration, 2.2 g, m.p. 192°-195°; m/e 237. cf J. Prakt. Chem. 135: 345-360 (1932); J. Med. Chem. 8: 637 (1965). The mixture was heated 5 minutes cooled to 25° crushed ice

反应条件: temp:160.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of commercially available 1-phenyl-1H-indole-2,3-dione (10.10 g, 45.7 mmol) in ethylene glycol (125 mL) is added powdered potassium hydroxide (7.4 g, 112 mmol), hydrazine hydrate (16.35 mL) and water (4 mL). The reaction is heated to 160° C. for 1.5 hr after which it is cooled to room temperature, made acidic with conc. hydrochloric acid, diluted with water and the resulting solids are collected by filtration. The solid is washed with water, dissolved in dichloromethane, dried and the solvent removed to give the 1-phenyl-1H-indol-2-one (8.6 g, 90% yield) as a solid. is cooled to room temperature the resulting solids are collected by filtration The solid is washed with water dissolved in dichloromethane dried the solvent removed

反应条件: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Phosphorous oxychloride (50 mL, 538 mmol) is added slowly to a solution of DMF (50 mL) in dichloromethane (50 mL) maintaining the temperature at 5° C. After 30 min, a solution of 1-phenyl-1H-indol-2-one (25 g, 120 mmol) and pyridine (25 mL, 309 mmol) in chloroform (125 mL) is added and the reaction is stirred 48 hr at room temperature. The reaction is poured into ice water (600 mL) and the aqueous layer is separated and extracted with chloroform (3×200 mL). The combined organic layer and extracts is dried, filtered and concentrated. The solid residue is crystallized from ethanol to afford 2-chloro-1-phenyl-1H-indole-3-carboxaldehyde (12.0 g, 39.25% yield) as an orange solid. NMR (CDCl3) 10.21 (1H, s), 8.37 (1H, d), 7.60 (3H, m), 7.41 (2H, m), 7.38 (1H, t), 7.28 (1H, m), 7.10 (1H, d). A second crop (7.5 g, 24.5% yield) is obtained by concentration of the filtrate and chromatography the residue eluting with dichloromethane. the aqueous layer is separated extracted with chloroform (3×200 mL) The combined organic layer and extracts is dried filtered concentrated The solid residue is crystallized from ethanol

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound is prepared in accordance with the procedures described in Latrell, Bartmann, Granzier DE 2 707 268 (1978) as follows. A solution of diphenylamine (40 g, 237 mmol) and triethylamine (66.1 mL, 474 mmol) in toluene (65 mL) is added dropwise to a solution of chloroacetyl chloride (20.7 mL, 260 mmol) in toluene (40 mL) while cooling in an ice-water bath. The cold bath is removed and the reaction mixture is heated at 55-65° C. for 3 hr. The cooled reaction mixture is diluted with toluene (100 mL), filtered and the filtrate concentrated to give 2-chloro-N,N-diphenylacetamide (24.4 g, 42% yield) as a light brown solid. NMR (CDCl3) 7.56-7.19 (10H, m), 4.01 (2H, s). while cooling in an ice-water bath The cold bath is removed The cooled reaction mixture filtered the filtrate concentrated

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Potassium t-butoxide (1.63 g, 14.5 mmoles) and 5 ml absolute ethanol were heated to 80°. 1-Phenyl-2(1H, 3H)-indolone 2.09 g, 10 mmoles) was added, followed by ethyl formate (1.09 ml, 13.5 mmoles). The mixture was heated 5 minutes, cooled to 25°, and the nearly solid mass diluted with 50 ml H2O and crushed ice, acidified to pH 3 with 3N HCl and title product recovered by filtration, 2.2 g, m.p. 192°-195°; m/e 237. cf J. Prakt. Chem. 135:345-360 (1932); J. Med. Chem. 8:637 (1965). The mixture was heated 5 minutes cooled to 25° crushed ice