HCID 11265881, compound → HCID 86703255, compound

Participants

Reaction Steps

To 453 mg of 2-amino-5-methylphenyl 4-methylbenzene sulfonate was added 1.6 ml of 5N-hydrochloric acid, and a solution in which 146 mg of sodium nitrite was dissolved in 1 ml of water was added dropwise at 0° C., and stirred for 30 minutes. Then, a solution in which 736 mg of stannous chloride was dissolved in 0.8 ml of 5N-hydrochloric acid was added dropwise at 0° C. and stirred for 1 hour. The solvent was distilled off under reduced pressure, 3.2 ml of ethanol and 167 μl of acetyl acetone were added and heated at reflux for 2 hours. To the reaction mixture was added 50 ml of water, neutralized with a saturated sodium bicarbonate solution, and extracted with 80 ml of ethyl acetate. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and purified using silica gel column chromatography (hexane:ethyl acetate=2:1) to yield 199.6 mg of the title compound.

Provenance & Evidence