Hydrazine hydrate (1:1) → 3-(4-Fluoro-2-nitrophenoxy)propylamine

6.5 g of 2-[3-(4-fluoro-2-nitrophenoxy)propyl]isoindole-1,3-dione was suspended in ethanol (140 ml), and hydrazine hydrate (3.0 ml) was added to the resulting suspension. The mixture was stirred for 3.5 hours while heating under reflux. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. 13 ml of 5N sodium hydroxide aqueous solution was added to the residue, and the resulting mixture was extracted with dichloromethane. The organic layer was washed with a saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate. The resulting dry product was concentrated under reduced pressure to thereby obtain 4.03 g of oily red orange 3-(4-fluoro-2-nitrophenoxy)propylamine (yield: 100%).

1. temperaturewhile heating
2. temperatureunder reflux
3. concentrationconcentrated under reduced pressure
4. addition13 ml of 5N sodium hydroxide aqueous solution was added to the residue
5. extractionthe resulting mixture was extracted with dichloromethane
6. washThe organic layer was washed with a saturated sodium chloride solution
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationThe resulting dry product was concentrated under reduced pressure

ORD record

ord-7e80194cbb02405f861a23682b216de0

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045464B2