3-Iodoaniline → (3-Iodophenyl)hydrazine

A solution of sodium nitrite (13.2 g, 186 mmol) in water (65 mL) was added over 90 minutes to a cooled (˜0 degrees) mixture of 3-iodo-aniline (40.71 g, 182 mmol) in concentrated hydrochloric acid (80 mL), taking care to ensure that the temperature remained below 0 degrees). The mixture was stirred for 30 min and then filtered. To the filtrate was added dropwise a solution of tin(II) chloride dihydrate (142 g, 0.63 mol) in water, and then the mixture was stirred for 30 minutes with the temperature maintained below 0 degrees. The reaction mixture was placed in the refrigerator overnight and then filtered. The residue was washed with brine, then 1:1 petroleum ether/ether (750 mL) and then with 2:1 petroleum ether/ether (375 mL) and the washings were discarded. The remaining residue was dissolved in 5 M NaOH and ether, and the aqueous layer was extracted with ether. The combined ether layers were washed with water and brine, dried (sodium sulfate), filtered, and evaporated to give 3-iodo-phenylhydrazine (25.3 g, 53%) as a dark red viscous oil.

1. temperaturea cooled
2. customremained below 0 degrees
3. filtrationfiltered
4. stirringthe mixture was stirred for 30 minutes with the temperature
5. temperaturemaintained below 0 degrees
6. customwas placed in the refrigerator overnight
7. filtrationfiltered
8. washThe residue was washed with brine
9. dissolutionThe remaining residue was dissolved in 5 M NaOH
10. extractionether, and the aqueous layer was extracted with ether
11. washThe combined ether layers were washed with water and brine
12. dry with materialdried (sodium sulfate)
13. filtrationfiltered
14. customevaporated

ORD record

ord-c9efac5af2324d61b2c19152f832afb4

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622492B2