Hydrochloric Acid → HCID 13575670, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 50 ml of concentrated hydrochloric acid and 19.8 g of 1D was stirred, warmed to 80° C. and then allowed to stand at room temperature for 18 hours. Then 50 ml of ice water was added, the mixture was cooled to 0° C. and stirred while a solution of 9.6 g of sodium nitrite in 20 ml of water was added drop-by-drop over 15 minutes. The cold mixture was stirred for an additional hour and then added to a cold stirred mixture of 100 g of sodium sulfite in 180 ml of water. The resulting mixture was stirred at room temperature for six hours, then 21.9 g of sodium dithionite was added, in portions. The resulting mixture was stirred at room temperature for 18 hours, then at 75° C. while 150 g of potassium chloride was added. The resulting mixture was stirred at 75° C. for 30 minutes, at room temperature for two hours, then was cooled to 5° C. and filtered. The filter cake was air dried, then mixed with 400 ml of methanol, the mixture was chilled to 0° C. and an excess of anhydrous hydrogen chloride was added. The methanol was evaporated under reduced pressure, the residue was taken up in water, 50% aqueous sodium hydroxide solution was added, and the resulting mixture was extracted with ether. The extract was dried (MgSO4) and the solvent was evaporated to give 2,3-dihydro-2,4-dimethyl-7-hydrazinobenzofuran (1E), as an amber syrup.

Provenance & Evidence