反应详情

温度

60 °C

To a suspension of 0.44 g (60% in oil, 0.011 mole) of sodium hydride in 10 ml of dimethylformamide was added 1.55 g (0.01 mole) of 5-fluoro-2-hydroxybenzamide in 10 ml of dimethylformamide under nitrogen atmosphere at room temperature. The reaction mixture was heated to 60° C. and 1.80 g (0.01 mole) of 1-methyl-3-pyrrolidinol methane sulfonate (ester) was added. The reaction mixture was then heated to 100° C. for 18 hr. The dimethylformamide was removed by rotary evaporation at 70° C., 0.5 mm Hg. The residue was taken up in 200 ml of methylene chloride, washed with 2×50 ml of 1N sodium hydroxide and 50 ml of water. The organic phase was extracted with 2×50 ml of 1N hydrochloric acid. The combined aqueous extracts were washed with 50 ml of methylene chloride, made basic with concentrated sodium hydroxide and extracted into 2× 50 ml of methylene chloride. The combined organic extracts were dried over sodium sulfate, filtered and concentrated by rotary evaporation. The residual oil was crystallized from hexane to give 1.0 g of off-white crystals, m.p. 90°-93° C.

1. temperatureThe reaction mixture was then heated to 100° C. for 18 hr
2. customThe dimethylformamide was removed by rotary evaporation at 70° C.
3. washwashed with 2×50 ml of 1N sodium hydroxide and 50 ml of water
4. extractionThe organic phase was extracted with 2×50 ml of 1N hydrochloric acid
5. washThe combined aqueous extracts were washed with 50 ml of methylene chloride
6. extractionextracted into 2× 50 ml of methylene chloride
7. dry with materialThe combined organic extracts were dried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated by rotary evaporation
10. customThe residual oil was crystallized from hexane