[OH-].[K+].[OH:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:14])[NH:9]2.Br[CH2:16][CH2:17][Cl:18].[OH-].[Na+]>C(O)CC>[Cl:18][CH2:17][CH2:16][O:3][C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:14])[NH:9]2
Potassium hydroxide (20 g) was added to a solution of 3,4-dihydro-5-hydroxycarbostyril (32.5 g) in propanol (250 mL), and stirred at 50°-60° C. until complete dissolution. 1-bromo-2-chloroethane (30 g) was then added, and the mixture heated at reflux temperature for 15 hours. After cooling, the reaction mixture was poured into aqueous sodium hydroxide (2N, 500 mL). The crude product thus formed was isolated by filtration, then recrystallized from diisopropyl ether to yield 31 g of pure 5-(2-chloroethoxy)-3,4-dihydrocarbostyril.
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