Aluminium lithium hydride → 2-(4-Chloro-2-methoxyphenyl)ethanamine

Temperature

0 °C

(E)-4-chloro-2-methoxy-1-(2-nitrovinyl)benzene (245 mg, 1.15 mmol) was diluted with THF (1 mL), placed under nitrogen and cooled to 0° C. LAH (4588 μL, 4.59 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 174 μL of water, 174 μL of 15% NaOH and 522 μL water. After stirring for 1 hour, ethyl acetate and MgSO4 was added. The reaction mixture was filtered and concentrated to yield 2-(4-chloro-2-methoxyphenyl)ethanamine (160 mg, 0.862 mmol, 75.1% yield).

1. temperaturewarming to ambient temperature
2. temperatureThe reaction was cooled to 0° C.
3. customquenched with 174 μL of water, 174 μL of 15% NaOH and 522 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-9456bbda852849d593c390db04a6e8ff

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08716498B2