2-Iodoaniline → (2-Iodophenyl)hydrazine

Temperature

0 °C

21.9 g (100 mmol) o-iodophenyl amine was dissolved in 40 mL concentrated hydrochloric acid. At 0° C., 6.9 g (100 mmol) sodium nitrite (dissolved in 35 mL water) was added dropwise, and stirred at 0° C. for half an hour. Then, SnCl2.2H2O 64.7 g (300 mmol) (dissolved in 70 mL concentrated hydrochloric acid) was added dropwise slowly, and reacted for about 3 h until complete. It was filtered to obtain a white solid, washed with a saturated solution of sodium chloride, and then washed with a mixed solvent of petroleum ether and diethyl ether (1:1). Then, the solid was adjusted to be basic with sodium hydroxide solution. The solid impurity therein was filtered, the aqueous phase was extracted with dichloromethane several times, the organic phases combined, dried, rotate evaporated to dryness to obtain a colorless oil 10.3 g, at a yield of 44.0%.

1. customreacted for about 3 h until complete
2. filtrationIt was filtered
3. customto obtain a white solid
4. washwashed with a saturated solution of sodium chloride
5. washwashed with a mixed solvent of petroleum ether and diethyl ether (1:1)
6. filtrationThe solid impurity therein was filtered
7. extractionthe aqueous phase was extracted with dichloromethane several times
8. customdried
9. customrotate evaporated to dryness

ORD record

ord-ba65a172163c42eb8567bf2271d00387

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09233098B2