Acetone → HCID 53741968, compound

Participants

Reaction Conditions

Reaction Steps

2-Nitro-5-methoxytoluene (24.9 g, 149 mmol) was dissolved in a solvent mixture (150 ml) of isopropanol--methanol (2:1). To the solution, 10% palladium-on-carbon (500 mg) was added, followed by stirring at room temperature for 5 hours in the atmosphere of hydrogen. After the reaction, the catalyst was removed by filtration, and the filtrate was condensed. The resultant residue was combined with acetone (150 ml) and pyridine (14.2 ml), and the mixture was cooled to 0° C. and stirred. Cinnamoyl chloride (18.5 g, 111 mmol) was added thereto and the mixture was stirred overnight at room temperature. The reaction mixture was condensed, and the residue was dissolved in chloroform, followed by washing with water, 2N-HCl, and aqueous NaCl solution in this order. The washed material was dried and condensed to obtain 28.33 g of N-(4-methoxy-2methylphenyl)cinnamamide as colorless needles (71.2%).

Provenance & Evidence