Ammonium Chloride → HCID 58042501, compound

Participants

Reaction Steps

3-Chloro-2-(1,1,1,3,3,3-hexafluoropropan-2-yloxy)-5-nitropyridine (Preparation 51, 2.55 g, 7.9 mmol), ammonium chloride (2.50 g, 46.7 mmol) and iron powder (1.70 g, 30.4 mmol) were suspended in a mixture of ethanol (10 mL) and water (3 mL). The suspension was heated for 3 hours under reflux then allowed to cool to room temperature. The reaction mixture was filtered on a celite pad and washed with ethanol. The filtrate was concentrated in vacuo and the residue partitioned between water and EtOAc. The aqueous layer was further extracted with EtOAc (2×25 mL). The combined organics were dried over magnesium sulfate and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 50% diethyl ether in heptane to afford the title compound as a light yellow oil (2.0 g, 87%).

Provenance & Evidence