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

A solution of 4-chloro-2-methyl-1-(2-nitrovinyl)benzene (1.83 g, 9.26 mmol) in tetrahydrofuran (40 mL) was cooled to 0° C. in an ice bath, and a 1M solution of lithium aluminum hydride in tetrahydrofuran (37 mL, 37 mmol) was added, dropwise over 10 minutes. The resulting mixture was stirred in the ice bath for 2 hours 30 minutes, then quenched in the following manner: water (1.5 mL) was added dropwise, and after stirring for 5 minutes, 1M sodium hydroxide (1.5 mL) was added. After stirring for a further 15 minutes, water (5 mL) was added, and the resulting mixture was stirred at ambient temperature for 15 minutes, then filtered through a medium porosity sintered glass funnel. The collected precipitate was washed with ethyl acetate (60 mL). The combined filtrate and wash was dried over sodium sulfate and concentrated to afford 2-(4-chloro-2-methylphenyl)ethanamine as a brown oil (1.17 g, 75% yield).

1. customquenched in the following manner
2. additionwater (1.5 mL) was added dropwise
3. addition1M sodium hydroxide (1.5 mL) was added
4. stirringAfter stirring for a further 15 minutes
5. additionwater (5 mL) was added
6. stirringthe resulting mixture was stirred at ambient temperature for 15 minutes
7. filtrationfiltered through a medium porosity sintered glass funnel
8. washThe collected precipitate was washed with ethyl acetate (60 mL)
9. washThe combined filtrate and wash
10. dry with materialwas dried over sodium sulfate
11. concentrationconcentrated

ORD record

ord-cbfe2d09d0b343b697b31f08d1d394bc

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569522B2