2,6-Dichloroaniline → (2,6-Dichlorophenyl)hydrazine monohydrochloride

Temperature

5 °C

To a cold solution of 2,6-dichloroaniline (10.0 g, 61.72 mmol) in conc. HCl was added aqueous solution of sodium nitrite (5.11 g, 74.00 mmol) at −15° C. The reaction mass was stirred at 0-10° C. for 15 minutes. The reaction mass was filtered off to remove insolubles and stannous chloride in conc. HCl (34.7 g, 150 mmol) was added to the filtrate. The reaction mass was further stirred at −15° C. for 30 min and filtered to afford 15.00 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 7.18-7.28 (m, 1H), 7.39-7.52 (m, 2H), 10.30 (br s, 3H); MS (m/z): 176.90 (M)+.

1. filtrationThe reaction mass was filtered off
2. additionwas added to the filtrate
3. stirringThe reaction mass was further stirred at −15° C. for 30 min
4. filtrationfiltered

ORD record

ord-b7381159b1e94cf8b9bafa5a24b9cfce

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09439890B2