Sulfuric Acid → HCID 69313521, compound

Participants

Reaction Conditions

Reaction Steps

Add a solution of 0.58 g (8.45 mmol) of sodium nitrite in 3 mL of water to a mixture of the aniline (1.66 g, 8.45 mmol), 19 mL of water and 5 mL of concentrated sulfuric acid cooled at 5° C. in an ice bath, while maintaining the temperature below 10° C. Stir the mixture for 30 min and pour the solution into a solution of 1.75 g (10.56 mmol) of potassium iodide in 10 mL of water. Heat the aqueous solution at 60° C. for 3 h. Cool the black solution and add chloroform. Separate the organic layer and wash with 10% sodium hydroxide, 1M sodium thiosulfate, 10% hydrochloric acid, water, saturated sodium bicarbonate and brine. Dry the organic layer over MgSO4, filter, concentrate the solvent under reduced pressure and chromatograph the residue using Hex/EtOAc 98:2 to provide 1-(5-chloro-2-iodo-phenyl)-pyrrolidine (60% yield). From this material, prepare the title compound using a procedure similar to Preparation 1.

Provenance & Evidence