Acetic Acid → N-(7-n-butyloxy-1,3,4,9-tetrahydro-2H-carbazol-2-yl)acetamide

Participants

Reaction Steps

A mixture of 0.2 mol of 3-n-butyloxyphenylhydrazine, 0.2 mol of N-(3-oxocyclohexyl)acetamide, and 350 ml of glacial HOAc was stirred at room temperature for 3 hr and then refluxed for 2 hr. After pouring into 2.5 l of H2O and stirring overnight, the insoluble material had partly crystallized. The crystalline material was filtered, washed with H2O, and dried (23 g, Fraction A). The remaining insoluble semi-solid was taken up in EtOAc, washed with H2O, dried, and evaporated. The dark residue was triturated with Et2O and filtered (6.7 g, mp 181°-183°, Fraction B). Additional product was extracted from Fraction A by stirring with two 4 l. portions of Et2O. The combined extracts were evaporated and the resulting residue combined with Fraction B and recrystallized twice from Me2CO to yield 10.2 g of the title compound, mp 182°-184°.

Provenance & Evidence