ethyl 12-aminododecanoate hydrochloride

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

实验步骤: Ethyl 12-aminododecanoate hydrochloride was prepared from 12-aminododecanoic acid, thionyl chloride, and ethanol by the general method of C. Temple, Jr., R. D. Elliott, and J. A. Montgomery, J. Med. Chem., 1988, 31, 697-700. The general method described in Step 1 of Example 15 was used to react 4-chloro-3-nitroquinoline (15.5 g, 74.4 mmol), ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol), and triethylamine (18.8 g, 186 mmol) in dichloromethane for 15 hours to provide ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate (30.0 g) as a yellow solid that was used directly in the next step without further purification.

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

实验步骤: 4-Chloro-3-nitroquinoline (15.52 g, 74.40 mmol) was treated with ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol) in the presence of potassium carbonate (10.28 g, 74.38 mmol) and triethylamine (25.9 mL, 186 mmol) according to a modification of the method described in Part A of Example 15. After the reaction was stirred for six hours, an analysis by TLC indicated the presence of starting material, and additional ethyl 12-aminododecanate hydrochloride (1.0 g, 3.6 mmol) was added. The reaction was stirred overnight and subjected to the work-up procedure to provide 31.0 g of ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate. was added The reaction was stirred overnight

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethanol (150 mL) was cooled to 0° C., and thionyl chloride (16.57 mL, 139.3 mmol) was added over a period of ten minutes. The reaction was stirred for ten minutes at 0° C., and 12-aminododecanoic acid (25.0 g, 116 mol) was then added. The reaction was allowed to warm to ambient temperature, stirred at a slightly elevated temperature for one hour, and stirred at ambient temperature for two hours. The Ethanol was removed under reduced pressure, and the solid residue was recrystallized from ethyl acetate. The crystals were isolated by filtration, washed with diethyl ether, and dried under vacuum to provide 37.4 g of ethyl 12-aminododecanoate hydrochloride as a white solid. to warm to ambient temperature stirred at a slightly elevated temperature for one hour stirred at ambient temperature for two hours The Ethanol was removed under reduced pressure the solid residue was recrystallized from ethyl acetate The crystals were isolated by filtration washed with diethyl ether dried under vacuum

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethanol (150 mL) was cooled to 0° C., and thionyl chloride (16.57 mL, 139.3 mmol) was added over a period of ten minutes. The reaction was stirred for ten minutes at 0° C., and 12-aminododecanoic acid (25.0 g, 116 mol) was then added. The reaction was allowed to warm to ambient temperature, stirred at a slightly elevated temperature for one hour, and stirred at ambient temperature for two hours. The Ethanol was removed under reduced pressure, and the solid residue was recrystallized from ethyl acetate. The crystals were isolated by filtration, washed with diethyl ether, and dried under vacuum to provide 37.4 g of ethyl 12-aminododecanoate hydrochloride as a white solid. to warm to ambient temperature stirred at a slightly elevated temperature for one hour stirred at ambient temperature for two hours The Ethanol was removed under reduced pressure the solid residue was recrystallized from ethyl acetate The crystals were isolated by filtration washed with diethyl ether dried under vacuum

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethanol (150 mL) was cooled to 0° C., and thionyl chloride (16.57 mL, 139.3 mmol) was added over a period of ten minutes. The reaction was stirred for ten minutes at 0° C., and 12-aminododecanoic acid (25.0 g, 116 mol) was then added. The reaction was allowed to warm to ambient temperature, stirred at a slightly elevated temperature for one hour, and stirred at ambient temperature for two hours. The Ethanol was removed under reduced pressure, and the solid residue was recrystallized from ethyl acetate. The crystals were isolated by filtration, washed with diethyl ether, and dried under vacuum to provide 37.4 g of ethyl 12-aminododecanoate hydrochloride as a white solid. to warm to ambient temperature stirred at a slightly elevated temperature for one hour stirred at ambient temperature for two hours The Ethanol was removed under reduced pressure the solid residue was recrystallized from ethyl acetate The crystals were isolated by filtration washed with diethyl ether dried under vacuum

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

实验步骤: Ethyl 12-aminododecanoate hydrochloride was prepared from 12-aminododecanoic acid, thionyl chloride, and ethanol by the general method of C. Temple, Jr., R. D. Elliott, and J. A. Montgomery, J. Med. Chem., 1988, 31, 697-700. The general method described in Step 1 of Example 15 was used to react 4-chloro-3-nitroquinoline (15.5 g, 74.4 mmol), ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol), and triethylamine (18.8 g, 186 mmol) in dichloromethane for 15 hours to provide ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate (30.0 g) as a yellow solid that was used directly in the next step without further purification.

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

实验步骤: Ethyl 12-aminododecanoate hydrochloride was prepared from 12-aminododecanoic acid, thionyl chloride, and ethanol by the general method of C. Temple, Jr., R. D. Elliott, and J. A. Montgomery, J. Med. Chem., 1988, 31, 697-700. The general method described in Step 1 of Example 15 was used to react 4-chloro-3-nitroquinoline (15.5 g, 74.4 mmol), ethyl 12-aminododecanoate hydrochloride (25.0 g, 89.3 mmol), and triethylamine (18.8 g, 186 mmol) in dichloromethane for 15 hours to provide ethyl 12-(3-nitroquinolin-4-ylamino)dodecanoate (30.0 g) as a yellow solid that was used directly in the next step without further purification.