Water → HCID 68867939, compound

Participants

Reaction Conditions

Reaction Steps

Cool a mixture of (2,2-dimethylpropyl)-(3-nitro-6-phenylethynylpyridin-2-yl)amine (3.11 g, 10 mmol), NaHCO3 (0.420 g, 5.0 mmol), MgSO4 (2.40 g, 20 mmol) in acetone (85 mL), and water (25 mL) and cool to 0° C. Add KMnO4 (3.16 g, 20.0 mmol) to the cooled mixture, and stir the reaction mixture vigorously at 0° C. for about 1-2 h. Quench the mixture with Na2SO3 (5.67 g, 45 mmol). Remove ice bath and stir mixture at RT for 2 h. Filter the solid through a pad of filtering agent. Wash with water (2×50 mL) and EtOAc (50 mL). Separate the phases and extract the aqueous phase with EtOAc (3×50 mL). Wash the combined organic phases with saturated aqueous NaCl (25 mL), dry with MgSO4, filter and concentrate. Purify the crude (silica gel chromatography, eluting with 1:1 hexanes:CH2Cl2) to give the title compound (1.586 g, 46%).

Provenance & Evidence