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(R)-(+)-2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy}propionic acid[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
Example 7. Preparation of Compound of Formula (I): (2R)-2-{4-[(7-Bromoquinolin-2- yl)oxy]phenoxy}propionic acid. An inerted rector equipped with a mechanical stirrer, a reflux condenser and a temperature probe was charged with 7-bromo-2-chloroquinoline (0.9225 Kg, 3.81 mole), of R-(+)-2-(4-hydroxy-phenoxy) propionic acid (0.721 Kg, 3.81 mole), potassium carbonate (1.319 Kg, 9.48 mole, 2.5 equiv.), and anhydrous dimethylformamide (4.254 Kg) with stirring at 200-300 rpm. The reaction mixture was then heated to 130 to 140C over a period of 1 hour. A temperature of 130 to 14O0C was maintained for a period of 15 hours. The reaction mixture was cooled to 15 to 200C when it became thick. The reactor was then charged with USP purified water (13.84 Kg) and treated slowly by addition of concentrated HCl (834.7 g). At the end of the addition of HCl, a precipitate was observed, and the pH of the mixture was between pH 3 to 4. The solid was extracted with ethyl acetate (8 L), and the ethyl acetate extract was washed with USP purified water (2 x 2L), followed by two washes with 10% citric acid solution. The ethyl acetate solution was then treated with 100 g of Darco G-60 charcoal and stirred for 30 minutes at 22C and filtered through a 10 micron polypropylene filter. The ethyl acetate extract thus obtained was distilled off at reduced (100 mm Hg) pressure. After .4 of the volume of ethyl acetate had distilled out, 6 L of isopropyl alcohol were added and the distillation was continued until another Vi volume of ethyl acetate distilled off. 4 Kg of USP purified water were then added slowly, and cooling was applied at10C/hour to reach a final temperature of 22C. The product crystallized out of the solution. The product was filtered through a polypropylene filter. The wet cake was dried in an isolator at 4O0C in a vacuum oven. The final yield of desired product was 0.753 Kg. A manual sieving was performed though a polyethylene sieve. Yield: 50%.
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