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a) 11.3 g of tin dichloride dihydrate are added to 2.25 g of <strong>[134610-32-5]3',4'-dimethoxy-5'-nitroacetophenone</strong> dissolved in 50 ml of ethanol, whereupon the mixture is stirred at 74 for 30 minutes. Thereupon, the reaction mixture is poured on to 100 g of ice, neutralized with about 300 ml of saturated sodium hydrogen carbonate solution and treated with 150 ml of methylene chloride. The mixture is filtered and the methylene chloride phase is separated. This is dried over sodium sulfate and evaporated, and the residue is recrystallized from ether/petroleum ether. There is obtained 5'-amino-3',4'-dimethoxyacetophenone of m.p. 63-65.
b) A solution of 5.2 g of sodium nitrile in 20 ml of water is added dropwise at 0 within 20 minutes to 14.0 g of <strong>[134611-49-7]5'-amino-3',4'-dimethoxyacetophenone</strong> dissolved in 155 ml of 1N hydrochloric acid. After stirring at -2 for 30 minutes the cold diazonium salt solution is added dropwise within 30 minutes at 5-10 to a solution of 8.7 g of copper(I) cyanide and 5.45 g of potassium cyanide in 60 ml of water. After completion of the addition 200 ml of methylene chloride are added, and the reaction mixture is stirred at 23 for 3 hours and then filtered. The organic phase is separated, washed with water, dried over sodium sulfate and evaporated. The residue is recrystallized from methylene chloride/petroleum ether. There is obtained 5'-cyano-3',4'-dimethoxyacetophenone of m.p. 125-126.
Taking compound 18 b (2.95 g, 10 mmol), dissolved in 20 ml dichloromethane in, stirring next adds by drops 5 ml trifluoroacetic acid, the reaction 2 - 3 H-. Water washing after completion of the reaction, methylene chloride extraction combined with the organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure, separating by silica gel column (dichloromethane: methanol=100:1), to obtain white solid compound 18 c (1.52 g, yield 78%).
Taking compound Apo - CHO (1.94 g, 10 mmol), dissolved in methanol, the compound is added under stirring 18 c (2.15 g, 11 mmol), the reaction 1 h, to not produce the yellow precipitate, added under mixing an appropriate amount of sodium, dropping of a catalytic amount of glacial acetic acid, the reaction at room temperature 2 h, water washing, extracted with ethyl acetate, the combined organic layer, drying with anhydrous sodium sulfate, concentrated under reduced pressure, separating by silica gel column (ethyl acetate: petroleum ether=1:4), which forms light brown solid compound JJA - D18 (2.05 g, yield 55%).
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