2-Iodoaniline → HCID 12326100, compound

Temperature

0 °C

2-Iodoaniline (16 g, 73 mmol) was suspended in concentrated hydrochloric acid (100 mL), and then cooled to 0° C. in an ice bath. Sodium nitrite (6 g, 87.6 mmol) in water (25 mL) was added slowly to reaction mixture and then reaction allowed to stir at 0° C. for 1.5 hours. In a separate flask, tin (II) chloride (84.7 g, 182.5 mmol) was dissolved in concentrated hydrochloric acid (12 mL) and added slowly over 30 minutes to reaction mixture. The resulting suspension was allowed to warm to room temperature and stirred for 14 h. The solid was filtered off, and allowed to dry to afford 1-(2-iodophenyl)hydrazine hydrochloride (19 g, 96%). 1H NMR (CDCl3, 300 MHz) δ 7.82 (dd, 1H, J=1.1, 7.7 Hz), 7.39 (dt, 1H, 1.2, 7.7 Hz), 6.96 (dd, 1H, J=1.1, 8.1 Hz), 6.82 (dt, 1H, J=1.1, 7.5) ppm. MS (ApCI) 275 (M++CH3CN+H).

1. customreaction
2. additionadded slowly over 30 minutes to reaction mixture
3. temperatureto warm to room temperature
4. stirringstirred for 14 h
5. filtrationThe solid was filtered off
6. customto dry

ORD record

ord-b57db802383b45f4b0fcc93c581c3c2a

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592454B2