Ammonium Chloride → (+/-)-3-(3-Aminophenyl)-5-(2,6-dichlorophenyl)-2-isoxazoline

Iron powder (99 mg, 1.78 mmol) was added into a suspension of (±)-5-(2,6-dichlorophenyl)-3-(3-nitrophenyl)-2-isoxazoline (100 mg, 0.297 mmol) in ethanol/water (2/1) under nitrogen. The mixture was stirred for 10 min, followed by the addition of ammonium chloride (32 mg, 0.594 mmol). The reaction was stirred for 20 min at room temperature, followed by heating at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and filtered through a plug of Celite. The filtrate was concentrated. The residue was dissolved in ethyl acetate and washed with aqueous sodium bicarbonate solution. The ethyl acetate layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel, eluting with 8:2 hexanes-ethyl acetate to provide the title compound as a light yellow solid.

1. stirringThe reaction was stirred for 20 min at room temperature
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationfiltered through a plug of Celite
4. concentrationThe filtrate was concentrated
5. dissolutionThe residue was dissolved in ethyl acetate
6. washwashed with aqueous sodium bicarbonate solution
7. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe resulting residue was purified by column chromatography on silica gel
11. washeluting with 8:2 hexanes-ethyl acetate

ORD record

ord-6456801a2c2d40c28209e30cae4de906

Source dataset

uspto-grants-2008_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07326790B2