2-chloro-1-[(E)-2-nitroethenyl]-4-(trifluoromethyl)benzene → 2-(2-Chloro-4-(trifluoromethyl)phenyl)ethanamine

Temperature

0 °C

(E)-2-chloro-1-(2-nitrovinyl)-4-(trifluoromethyl)benzene (160 mg, 0.636 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (2544 μL, 2.54 mmol) was added dropwise and the reaction was stirred for 5 hours warming to ambient temperature. The reaction was cooled to 0° C. and quenched with 100 μL of water, 100 μL of 15% NaOH and 300 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(2-chloro-4-(trifluoromethyl)phenyl)ethanamine (60 mg, 0.268 mmol, 42.2% yield).

1. temperaturewarming to ambient temperature
2. temperatureThe reaction was cooled to 0° C.
3. customquenched with 100 μL of water, 100 μL of 15% NaOH and 300 μL water
4. stirringAfter stirring for 1 hour
5. additionethyl acetate and MgSO4 was added
6. filtrationThe reaction mixture was filtered
7. concentrationconcentrated

ORD record

ord-f272dbcff26141deab7da81bdee93885

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569522B2