Process for producing carbostyril derivatives
a technology of carbostyril and derivatives, which is applied in the field of process for producing carbostyril derivatives, can solve the problems of complex purification process of compound of general formula (i) and achieve the effect of high yield and high purity
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example 1
[0025] Into a three-necked flask having a capacity of 300 ml were introduced 10.00 g of 6-hydroxy-3,4-dihydrocarbostyril, 16.36 g of 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole, 10.16 g of potassium carbonate, 3.00 g of tetrabutylammonium chloride, 0.05 g of sodium sulfite, 30 ml of toluene and 50 ml of water. The content of the flask was heated under reflux for 8 hours with stirring. After cooling the reaction mixture to ambient temperature, the deposited crystalline product was collected by filtration and washed with 50 ml of water. Then, the crude crystal thus obtained was introduced into 70 ml of 90% methanol cooled to 5° C., and stirred at 5° C. for 10 minutes for the sake of washing. The crystal was collected by filtration and further washed on the suction filter with 20 ml of 90% methanol cooled to 5° C. The crystal was dried to obtain 21.46 g (yield 95%) of 6-[4-(1-cyclohexyl-1,2,3,4-tetrazol-5-yl)butoxy]-3,4-dihydrocarbostyril as a colorless needle-like crystalline pro...
example 2
[0033] Into a flask having a capacity of 200 ml were introduced 12.00 g of 6-hydroxy-3,4-dihydrocarbostyril, 19.60 g of 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole, 8.20 g of 50% aqueous solution of tetrabutylammonium chloride, 12.20 g of potassium carbonate, 0.60 g of sodium sulfite and 60 ml of water. The content of the flask was heated under reflux for 8 hours with stirring. After the reaction, the reaction mixture was cooled to ambient temperature, and the deposited crude crystal was once collected by filtration. After washing the crystal firstly with 36 ml of methanol and then with 60 ml of water, the crystal was again introduced into a flask having a capacity of 200 ml and heated under reflux together with 84 ml of methanol for 2 hours. The solution thus obtained was cooled to 10° C. The crystal was collected by filtration, washed firstly with 24 ml of methanol and then with 24 ml of water, and dried at 80° C. Thus, 23.84 g (yield 87.7%) of 6-[4-(1-cyclohexyl-1,2,3,4-tetr...
example 3
[0036] Into a reaction vessel having a capacity of 100 L were introduced 5 kg of 6-hydroxy-3,4-dihydrocarbostyril (30.64 mol), 8.2 kg of 1-cyclohexyl-5-(4-chlorobutyl)-1,2,3,4-tetrazole (33.78 mol), 4.7 kg of potassium carbonate (34.01 mol), 1.0 kg of sodium hydroxide (25 mol), 3.5 kg of 50% aqueous solution of tetrabutylammonium chloride (6.30 mol), 0.25 kg of sodium sulfite (1.98 mol), and 25 L of water. The mixture of the reactants was heated at 85° C. (80-90° C.) for 6 hours with circulating by continuous disperser (pipeline homomixer PL-SL manufactured by TOKUSHUKIKA KOGYO CO. LTD.). After the completion of the reaction, the reaction mixture was cooled to around 50° C. and 15 L of methanol were added thereinto. The reaction mixture with methanol was heated under reflux for 30 minutes. The obtained reaction mixture was cooled to 10 to 20° C. for 30 minutes or more, and the crystals were separated out. The obtained crystals were washed with 25 L of water, 15 L of methanol, and 25...
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