Sodium Hydroxide → HCID 117601300, compound

Participants

Reaction Steps

Crude N-(4-(3,5-dimethylisoxazol-4-yl)-2-iodo-6-nitrophenyl)-N-ethyl-2,2,2-trifluoroacetamide (1.5 g, 3.1 mmol) was dissolved in 100 mL of methanol. To the mixture was added 1M sodium methoxide in methanol (15.5 mL, 15.5 mmol) and reaction stirred at room temperature until complete. Reaction was then quenched with 15 mL of 1M HCl or until pH is approximately neutral then diluted with aqueous ammonium chloride. Methanol was removed under reduced pressure and then remaining suspension was extracted with EtOAc. The solution was washed with water, brine then dried over sodium sulfate. Solvents were removed under reduced pressure the residue was then dissolved in 20 mL of ethanol and placed in a sealed pressure tube with stannous chloride (2.2 g, 11.62 mmol). The mixture was heated at 120° C. for 1 hour. Reaction mixture was cooled to room temperature. To the mixture was added 1M NaOH (10 mL) and the mixture was stirred at room temperature for 30 minutes. At this point the reaction mixture was diluted with water and extracted with EtOAc (3 times). The solution was washed with water, brine and dried over sodium sulfate. Solvents were removed under reduced pressure and crude product was purified by silica gel chromatography (Hexanes/EtOAc as the eluent) to provide 4-(3,5-dimethylisoxazol-4-yl)-N1-ethyl-6-iodobenzene-1,2-diamine (310 mg, 22%).

Provenance & Evidence