HCID 18923472, compound → 3,5-Dichloro-N-methylaniline

To a stirred solution of 3',5'-dichloro-N-methylbenzanilide (2.317 g) in tetrahydrofuran was added lithium aluminum hydride (380 mg) in an ice-bath and the resulting suspension was stirred at the same temperature for one hour. The reaction mixture was quenched with saturated ammonium chloride and filtered through celite pad. The inorganic material on the celite was washed with ethyl acetate. Methanol was added to the filtrate and stirred at ambient temperature for half an hour. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-n-hexane (1:9, V/V) to afford 3,5-dichloro-N-methylaniline (1.38 g) as a colorless oil.

1. customThe reaction mixture was quenched with saturated ammonium chloride
2. filtrationfiltered through celite pad
3. washThe inorganic material on the celite was washed with ethyl acetate
4. additionMethanol was added to the filtrate
5. stirringstirred at ambient temperature for half an hour
6. washThe organic layer was washed with water
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated in vacuo
9. customThe residue was purified by flash chromatography
10. washeluting with ethyl acetate-n-hexane (1:9, V/V)

ORD record

ord-e9f84849f52d4c6eab84594ffb8786c7

Source dataset

uspto-grants-1996_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05574042