20168-99-4

Cindomet,Chiesi

ChEBI: Cinmetacin is a member of indole-3-acetic acids.

6.0 g of cinnamoyl chloride was dropwise added to a mixture of 8.7 g of pmethoxyphenylhydrazine hydrochloride, 10.1 g of triethylamine and 200 ml of toluene under cooling at -5° to 0°C. The reaction mixture was stirred at 20°- 25°C for 1 h. The separated precipitates were filtered off and dry gaseous hydrogen chloride was introduced into the filtrate. As a result a large amount of crystals of N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine hydrochloride were produced. These crystals were collected by filtration and washed with 20 ml of ether and dried to yield N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine hydrochloride of melting point 183°-185°C.
A mixture of N1-cinnamoyl-N1-(p-methoxyphenyl)hydrazine hydrochloride and
acetonylmalonic acid was heated in acetic acid at heating with stirring. Thereafter, the reaction mixture was allowed to cool, and was poured into cold water, and then crystals were produced. They were collected by filtration, and dried to give crude product. The recrystallization from acetone-water gave fine white needle crystals of 1-cinnamoyl-2-methyl-5-methoxy-3-indolylacetic acid, melting point 164°-165°C.

Antiinflammatory