Hydrochloric Acid → 1-(pyridin-3-ylmethyl)-1H-indazol-4-amine

Participants

Reaction Steps

To a vial containing 3-iodo-4-nitro-1-(pyridin-3-ylmethyl)-1H-indazole (0.145 g, 0.381 mmol) was added THF (2.4 mL) and MeOH (1.2 mL). To this solution was added Zn dust (0.249 g, 3.81 mmol) followed by HCl (2.54 mL, 7.63 mmol, 3.0 M aqueous). The mixture was stirred for 1.0 hours. The mixture was filtered through GF/F paper and the collected solids were washed with CHCl3 (30 mL). A saturated aqueous KOAc solution was added to the filtrate until the pH was neutral and then a saturated aqueous Rochelle's Salt solution was added. The mixture was stirred vigorously, the layers were separated and the aqueous phase was extracted with CHCl3. The combined organic extracts were washed with brine and dried over Na2SO4, filtered and concentrated. The product was purified by column chromatography (1 to 10% MeOH/CH2Cl2) to afford the product as a thick oil (0.041 g, 47%).

Provenance & Evidence