2-Methyl-2,3-dihydrobenzofuran-7-aMine

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 157 ml of concentrated hydrochloric acid and 66.1 g of 1C was stirred at room temperature for one hour, then 485 ml of water was added. The mixture was warmed to 70° C., then allowed to cool and stand at room temperature for 18 hours, then cooled to 5° C., while a solution of 33.7 g of sodium nitrite in 48 ml of water was added drop-by-drop (over 20 minutes). The resulting solution was stirred at 5° C. for 1 hour, then added drop-by-drop (over 10 minutes) to a stirred mixture of 393.5 g of sodium sulfite in 755 ml of water, at 5° C. The resulting mixture was stirred at room temperature for 2 hours, then a slurry of 77.2 g of sodium dithionite in 100 ml of water was added, in portions, to the stirred mixture. The mixture was stirred for 2 hours at room temperature, then at 70° C. for 15 minutes, when 1 pound of potassium chloride was added. The mixture was stirred at room temperature for 18 hours, cooled to 4° C. and filtered. 125 g of the resulting solid product was mixed with 500 ml of methanol. The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added. The mixture was stirred for 1 hour at 0° C., then most of the methanol was evaporated under reduced pressure at room temperature. The mixture was mixed with 500 ml of cold water, made basic by the addition of 50% aqueous sodium hydroxide solution, and extracted with ether. The extract was dried (MgSO4), and the solvent was evaporated to give 7-hydrazino-2,3-dihydro-2-methylbenzofuran (1D), as an amber syrup. The mixture was warmed to 70° C. to cool stand at room temperature for 18 hours was added drop-by-drop (over 20 minutes) The resulting solution was stirred at 5° C. for 1 hour The resulting mixture was stirred at room temperature for 2 hours The mixture was stirred for 2 hours at room temperature at 70° C. for 15 minutes The mixture was stirred at room temperature for 18 hours cooled to 4° C. filtered 125 g of the resulting solid product was mixed with 500 ml of methanol The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added The mixture was stirred for 1 hour at 0° C. most of the methanol was evaporated under reduced pressure at room temperature The mixture was mixed with 500 ml of cold water made basic by the addition of 50% aqueous sodium hydroxide solution extracted with ether The extract was dried (MgSO4) the solvent was evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 81 g of 1B, 400 ml of tetrahydrofuran (THF) and 3 g of activated Raney nickel catalyst was shaken under 35 p.s.i.g. hydrogen pressure at room temperature for 4 hours. The resulting mixture was treated with 20 g of magnesium sulfate, filtered and the solvent was evaporated from the filtrate, to give 7-amino-2,3-dihydro-2-methylbenzofuran (1C), as an amber syrup. filtered the solvent was evaporated from the filtrate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 81 g of 1B, 400 ml of tetrahydrofuran (THF) and 3 g of activated Raney nickel catalyst was shaken under 35 p.s.i.g. hydrogen pressure at room temperature for 4 hours. The resulting mixture was treated with 20 g of magnesium sulfate, filtered and the solvent was evaporated from the filtrate, to give 7-amino-2,3-dihydro-2-methylbenzofuran (1C), as an amber syrup. filtered the solvent was evaporated from the filtrate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 81 g of 1B, 400 ml of tetrahydrofuran (THF) and 3 g of activated Raney nickel catalyst was shaken under 35 p.s.i.g. hydrogen pressure at room temperature for 4 hours. The resulting mixture was treated with 20 g of magnesium sulfate, filtered and the solvent was evaporated from the filtrate, to give 7-amino-2,3-dihydro-2-methylbenzofuran (1C), as an amber syrup. filtered the solvent was evaporated from the filtrate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound, MS: m/e=377.4 (M+H+), was prepared in accordance with the general method of example 14 from 2-chloro-6-nitro-quinoline, 2,3-dihydro-2-methyl-7-benzofuranamine (CAS 26210-74-2) and isopropyl isocyanate.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound, MS: m/e=292.0 (M+H+), was prepared in accordance with the general method of example 1 from 5-nitro-2-chloroquinoline and 2,3-dihydro-2-methyl-7-benzofuranamine (CAS 26210-74-2).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 157 ml of concentrated hydrochloric acid and 66.1 g of 1C was stirred at room temperature for one hour, then 485 ml of water was added. The mixture was warmed to 70° C., then allowed to cool and stand at room temperature for 18 hours, then cooled to 5° C. while a solution of 33.7 g of sodium nitrite in 48 ml of water was added drop-by-drop (over 20 minutes). The resulting solution was stirred at 5° C. for 1 hour, then added drop-by-drop (over 10 minutes) to a stirred mixture of 393.5 g of sodium sulfite in 755 ml of water, at 5° C. The resulting mixture was stirred at room temperature for 2 hours, then a slurry of 77.2 g of sodium dithionite in 100 ml of water was added, in portions, to the stirred mixture. The mixture was stirred for 2 hours at room temperature, then at 70° C. for 15 minutes, when 1 pound of potassium chloride was added. The mixture was stirred at room temperature for 18 hours, cooled to 4° C. and filtered. 125 g of the resulting solid product was mixed with 500 ml of methanol. The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added. The mixture was stirred for 1 hour at 0° C., then most of the methanol was evaporated under reduced pressure at room temperature. The mixture was mixed with 500 ml of cold water, made basic by addition of 50% aqueous sodium hydroxide solution, and extracted with ether. The extract was dried (MgSO4) and the solvent was evaporated to give 7-hydrazino-2,3dihydro-2-methylbenzofuran (1D), as an amber syrup. The mixture was warmed to 70° C. to cool stand at room temperature for 18 hours was added drop-by-drop (over 20 minutes) The resulting solution was stirred at 5° C. for 1 hour The resulting mixture was stirred at room temperature for 2 hours The mixture was stirred for 2 hours at room temperature at 70° C. for 15 minutes The mixture was stirred at room temperature for 18 hours cooled to 4° C. filtered 125 g of the resulting solid product was mixed with 500 ml of methanol The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added The mixture was stirred for 1 hour at 0° C. most of the methanol was evaporated under reduced pressure at room temperature The mixture was mixed with 500 ml of cold water made basic by addition of 50% aqueous sodium hydroxide solution extracted with ether The extract was dried (MgSO4) the solvent was evaporated

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound, MS: m/e=421.4 (M+H+), was prepared from 5-nitro-2-chloroquinoline, 2,3-dihydro-2-methyl-7-benzofuranamine (CAS 26210-74-2) and indole-4-carbaldehyde as described in example 26.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The title compound, MS: m/e=468.3 (M+H+), was prepared in accordance with the general method of example 89 from 5-nitro-2-chloroquinoline, 3,5-difluorobenzenesulfonylchloride and 2,3-dihydro-2-methyl-7-benzofuranamine (CAS 26210-74-2).

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 157 ml of concentrated hydrochloric acid and 66.1 g of 1C was stirred at room temperature for one hour, then 485 ml of water was added. The mixture was warmed to 70° C., then allowed to cool and stand at room temperature for 18 hours, then cooled to 5° C., while a solution of 33.7 g of sodium nitrite in 48 ml of water was added drop-by-drop (over 20 minutes). The resulting solution was stirred at 5° C. for 1 hour, then added drop-by-drop (over 10 minutes) to a stirred mixture of 393.5 g of sodium sulfite in 755 ml of water, at 5° C. The resulting mixture was stirred at room temperature for 2 hours, then a slurry of 77.2 g of sodium dithionite in 100 ml of water was added, in portions, to the stirred mixture. The mixture was stirred for 2 hours at room temperature, then at 70° C. for 15 minutes, when 1 pound of potassium chloride was added. The mixture was stirred at room temperature for 18 hours, cooled to 4° C. and filtered. 125 g of the resulting solid product was mixed with 500 ml of methanol. The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added. The mixture was stirred for 1 hour at 0° C., then most of the methanol was evaporated under reduced pressure at room temperature. The mixture was mixed with 500 ml of cold water, made basic by the addition of 50% aqueous sodium hydroxide solution, and extracted with ether. The extract was dried (MgSO4), and the solvent was evaporated to give 7-hydrazino-2,3-dihydro-2-methylbenzofuran (1D), as an amber syrup. The mixture was warmed to 70° C. to cool stand at room temperature for 18 hours was added drop-by-drop (over 20 minutes) The resulting solution was stirred at 5° C. for 1 hour The resulting mixture was stirred at room temperature for 2 hours The mixture was stirred for 2 hours at room temperature at 70° C. for 15 minutes The mixture was stirred at room temperature for 18 hours cooled to 4° C. filtered 125 g of the resulting solid product was mixed with 500 ml of methanol The resulting suspension was stirred at 0° C. while an excess of anhydrous hydrogen chloride was added The mixture was stirred for 1 hour at 0° C. most of the methanol was evaporated under reduced pressure at room temperature The mixture was mixed with 500 ml of cold water made basic by the addition of 50% aqueous sodium hydroxide solution extracted with ether The extract was dried (MgSO4) the solvent was evaporated