Stannous Chloride → 5-benzenesulfonyl-1H-indazol-3-ylamine

Participants

Reaction Conditions

Reaction Steps

2-Amino-5-benzenesulfonyl-benzonitrile (0.81 g, 3.15 mmol) in 37% HCl (5 mL) was treated dropwise at 4° C. with NaNO2 (261 mg, 3.78 mmol) in 5 mL of water. After 1.75 hours the suspension was added dropwise to a solution of SnCl2 (4.88 g, 25.21 mmol) in 5 mL of 37% HCl. After stirring at 4° C. for 3 hours the solid was filtered, taken up with water (30 mL) and boiled for 1.5 hours. The hot mixture was filtered and washed thoroughly with boiling water. The filtrate was cooled to 4° C. and treated under stirring with 17% NaOH (approximately 5 mL) dropwise. After overnight cooling in a fridge the solid was filtered and washed with water to neutral pH affording 0.348 g of title compound (40% yield).

Provenance & Evidence