3,6-dichloropyridazin-4-amine

Synthesis

General procedure for the synthesis of 3,6-dichloropyridazin-4-amine from 3,4,6-trichloropyridazine: Example 24A: 3,4,6-Trichloropyridazine (25 g, 136 mmol) was added to a 500 mL stainless steel pressure flask containing 14.8 N ammonium hydroxide solution (200 mL). The reaction mixture was stirred at 75°C for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solid product was collected by filtration to afford 17 g (76% yield) of the target compound 3,6-dichloropyridazin-4-amine. The product characterization data were as follows: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.16 (s, 2H), 6.82 (s, 1H); MS (ESI+) m/z 164 (M+H)+.

References

[1] Journal of Organic Chemistry, 2014, vol. 79, # 21, p. 10311 - 10322
[2] Patent: US2017/15675, 2017, A1. Location in patent: Paragraph 1001
[3] Patent: US2009/163489, 2009, A1. Location in patent: Page/Page column 51
[4] Patent: US2014/349990, 2014, A1. Location in patent: Paragraph 1051; 1052
[5] Patent: WO2014/191896, 2014, A1. Location in patent: Page/Page column 217; 218