反应详情

A solution of 2-(3-chloro-phenoxy)-nicotinic acid (0.25 grams, 1.0 mmole) in thionyl chloride (10 ml) was heated to reflux. After 1 hour the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The resulting residue was dissolved in tetrahydrofuran (5 ml) and added dropwise to a solution of (S)-2-hydroxy-1-phenyl ethylamine (0.14 grams, 1.0 mmole) in pyridine (5 ml) at 0° C. After 30 minutes the mixture was warmed to room temperature. After 1 hour the mixture was poured into 1 N hydrochloric acid and extracted with ethyl acetate. The combined organics were washed with 1 N hydrochloric acid followed by brine and dried over Na2SO4. Concentration under reduced pressure resulted in a yellow oil that was purified by chromatography on silica gel eluting with 1:1 ethyl acetate/hexane to give a colorless oil. Anal. calcd. for C20H17N2O3Cl: C, 65.13; H, 4.65; N, 7.60. Found: C, 65.20; H, 4.78; N, 7.38; M.S. m/z [M+] 369; 1H NMR (400 MHz, CDCl3) d 2.54 (s, broad, 1H), 3.95 (m, 2H), 5.32 (m, 1H), 7.23 (m, 10H), 8.22 (m, 1H), 8.58 (m, 2H).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in tetrahydrofuran (5 ml)
3. temperatureAfter 30 minutes the mixture was warmed to room temperature
4. extractionextracted with ethyl acetate
5. washThe combined organics were washed with 1 N hydrochloric acid
6. dry with materialdried over Na2SO4
7. concentrationConcentration under reduced pressure
8. customresulted in a yellow oil that
9. customwas purified by chromatography on silica gel eluting with 1:1 ethyl acetate/hexane
10. customto give a colorless oil