反应详情

温度

90 °C

To a suspension of morpholine-4-carboxylic acid [4-(2-fluoro-4-nitrophenoxy)pyridin-2-yl]amide (941 mg) in ethanol (50 ml) were added water (10 ml), electrolytic iron powder (581 mg), ammonium chloride (1.11 g) and N,N-dimethylformamide (0.75 ml), followed by stirring to heat at 90° C. for 30 min. The reaction mixture was cooled down to room temperature, and filtered to remove an insoluble portion, which was washed with water and N,N-dimethylformamide in this order. The filtrate was concentrated under a reduced pressure to give a residue, to which ethyl acetate (100 ml) and water (100 ml) were added to partition. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (Fuji Silysia NH, eluent; hexane:ethyl acetate=1:1 to 1:2, ethyl acetate, then ethyl acetate:methanol=20:1 to 10:1). Fractions containing the target compound were concentrated to provide the titled compound (759 mg, 87.8%) as a pale yellow oil.

1. temperatureThe reaction mixture was cooled down to room temperature
2. filtrationfiltered
3. customto remove an insoluble portion, which
4. washwas washed with water and N,N-dimethylformamide in this order
5. concentrationThe filtrate was concentrated under a reduced pressure
6. customto give a residue
7. customto partition
8. extractionThe aqueous layer was extracted with ethyl acetate
9. washThe combined organic layer was washed with water and brine in this order
10. dry with materialdried over anhydrous sodium sulfate
11. customThe solvent was evaporated under a reduced pressure
12. customto give a residue, which
13. customwas then purified by silica gel column chromatography (Fuji Silysia NH, eluent
14. additionFractions containing the target compound
15. concentrationwere concentrated