Sodium Hydroxide → cis-4-(3-Chlorophenyl)-but-3-enylamine

To a stirred suspension of (Z)-2-(4-(3-chlorophenyl)but-3-enyl)isoindoline-1,3-dione (8.4 g, 27 mmol) in ethanol (100 mL) at ambient temperature was added hydrazine monohydrate (65%, 2.6 mL, 54 mmol). The resulting mixture was stirred and heated to reflux, and a yellow solution formed upon attaining reflux. About 10 minutes after reflux began, a precipitate formed in the reaction mixture. After a total of 35 minutes at reflux, the precipitate nearly filled the flask, and the heat was removed. On reaching ambient temperature, the reaction mixture formed a solid mass. The mass was dissolved by adding of 2M sodium hydroxide (100 mL). The resulting solution was concentrated to remove most of the ethanol. The remaining cloudy mixture was extracted with ethyl acetate (100 mL). The aqueous layer turned into a gel and the organic layer was decanted away. The organic layer was washed with water (50 mL), then dried over sodium sulfate and concentrated to afford (Z)-4-(3-chlorophenyl)but-3-en-1-amine as a light brown oil (4.66 g, 95%).

1. temperatureheated
2. temperatureto reflux
3. customa yellow solution formed
4. temperatureupon attaining reflux
5. temperatureAbout 10 minutes after reflux
6. customa precipitate formed in the reaction mixture
7. temperatureAfter a total of 35 minutes at reflux
8. additionthe precipitate nearly filled the flask
9. customthe heat was removed
10. customOn reaching ambient temperature
11. customthe reaction mixture formed a solid mass
12. dissolutionThe mass was dissolved
13. concentrationThe resulting solution was concentrated
14. customto remove most of the ethanol
15. extractionThe remaining cloudy mixture was extracted with ethyl acetate (100 mL)
16. customthe organic layer was decanted away
17. washThe organic layer was washed with water (50 mL)
18. dry with materialdried over sodium sulfate
19. concentrationconcentrated

ORD record

ord-45bae3bed98e488d91c2ed466f8baa46

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096567B2