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With sodium hydroxide; boron tribromide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane;
III. Synthesis of 7-Hydroxyisoquinoline To a 2-liter, 3-necked round bottom flask equipped with a magnetic stir bar and addition funnel is added 19.7 g (0.124 mole) <strong>[39989-39-4]7-methoxyisoquinoline</strong> and 800 ml of dry dichloromethane. This solution is stirred and cooled to -75 C. with a dry ice/acetone bath, 628 ml (0.628 mole) of 1.0M boron tribromide in dichloromethane is added dropwise maintaining the temperature at -75 C. Thereafter the slurry is stirred for 18 hours allowing the temperature to rise to room temperature. The reaction slurry is poured into 1 liter of ice water and stirred for an hour. The layers are separated and the aqueous layer is then adjusted from acidic to neutral (pH 7) with 1N NaOH. A yellow solid precipitates and is filtered off, then air dried to yield 14.5 g of a yellow solid, 81%.
With pyridine hydrochloride; In ethyl acetate;
(15-1) The raw material <strong>[39989-39-4]7-methoxyisoquinoline</strong> was prepared according to J. Org. Chem., 38(21), 3701(1973). A mixture of 7.4 g of <strong>[39989-39-4]7-methoxyisoquinoline</strong> and 30 g of pyridine hydrochloride was heated with stirring at 180 for 6 hours. The reaction mixture was allowed to cool, dissolved in ethyl acetate, and washed with a saturated aqueous sodium chloride solution. The solution was dried with anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure to give 4.43 g of 7-hydroxyisoquinoline.
IV. Synthesis of 7-Hydroxy-8-nitroisoquinoline To a 300 ml round bottom flask is added 14.5 g (0.1 mole) of 7-hydroxyisoquinoline and 100 ml of warmed tetramethylene sulfone. The brown slurry is stirred and to it is added portionwise 18.6 g (0.14 mole) of nitronium tetrafluoroborate with cooling (ice bath). The reaction is stirred for 3 hours. The reaction is then quenched with 100 ml of methanol, evaporated to dryness and triturated twice with ether to precipitate a dark solid (19.0 g, 100%).
100%
With nitronium tetrafluoroborate; In methanol;
IV. Synthesis of 7-Hydroxy-8-nitroisoquinoline To a 300 ml round bottom flask is added 14.5 g (0.1 mole) of 7-hydroxyisoquinoline and 100 ml of warmed tetramethylene sulfone. The brown slurry is stirred and to it is added portionwise 18.6 g (0.14 mole) of nitronium tetrafluoroborate with cooling (ice bath). The reaction is stirred for 3 hours. The reaction is then quenched with 100 ml of methanol, evaporated to dryness and triturated twice with ether to precipitate a dark solid (19.0 g, 100%).
With sodium hydroxide; boron tribromide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane;
III. Synthesis of 7-Hydroxyisoquinoline To a 2-liter, 3-necked round bottom flask equipped with a magnetic stir bar and addition funnel is added 19.7 g (0.124 mole) of <strong>[39989-39-4]7-methoxyisoquinoline</strong> and 800 ml of dry dichloromethane. This solution is stirred and cooled to -75 C. with a dry ice/acetone bath, 628 ml (0.628 mole) of 1.0M boron tribromide in dichloromethane is added dropwise maintaining the temperature at -75 C. Thereafter the slurry is stirred for 18 hours allowing the temperature to rise to room temperature. The reaction slurry is poured into 1 liter of ice water and stirred for an hour. The layers are separated and the aqueous layer is then adjusted from acidic to neutral (pH 7) with 1N NaOH. A yellow solid precipitates and is filtered off, then air dried to yield 14.5 g of a yellow solid, 81%.
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