288-13-1

73781-91-6

321533-62-4

Example 7. Preparation of 0-(6-pyrazol-1-yl-pyridin-3-ylmethyl)-hydroxylamine (compound of Formula (XI)); Step 7a. Preparation of methyl 6-pyrazol-1-yl-nicotinate (compound of Formula (XI-a)); To a solution of pyrazole (19.4 g, 0.28 mol) dissolved in 100 mL of anhydrous DMSO (at temperature 0°C) was added, in one portion, over 30 minutes, a solution of pyrazole (19.4 g, 0.28 mol) dissolved in NaH (7.5 g, 0.3 mol). The reaction mixture was slowly warmed up to room temperature and stirred continuously at that temperature for 30 min. Subsequently, methyl 6-chloronicotinate (35 g, 0.2 mol) was added to the stirring reaction mixture and stirred vigorously for 6 hours. Upon completion of the reaction, the mixture was cooled to about 0 °C and slowly poured into pre-cooled saturated aqueous NH4Cl solution. The precipitate formed was collected by filtration, washed with water and dried to give the compound of formula (XI-a) (38.3 g, 93% yield) as an off-white solid.