n-Methyl-p-aminophenol → HCID 54163094, compound

Participants

Reaction Steps

A mixture of 62.5 grams (0.5 mole) of N-methyl-p-aminophenol, 74.0 grams (0.5 mole) of triethyl orthoformate, and 33.5 grams (0.5 mole) of malononitrile in 400 milliliters of 99.5% ethanol was prepared under a nitrogen atmosphere and heated at 75°-78° C. for 17 hours. The reaction mixture was cooled to room temperature, diluted with 1.5 liters of water plus ice and allowed to stand 1/2 hour. The precipitate was filtered to obtain 44 grams of α-cyano-β-(N-methyl-p-hydroxyanilino)acrylonitrile, melting point 187°-189° C. Five grams of this precipitate was treated with diethylsulfate in aqueous sodium hydroxide to obtain 0.5 gram of α-cyano-β-(N-methyl-p-ethoxyanilino)acrylonitrile (Formula II, supra) as a solid which melts at 147°-148° C. after recrystallization from ethyl acetate.

Provenance & Evidence