Reaction #2276

Reaction equation

N-(4-chlorophenyl)cinnamamide

aluminum chloride

→

5-chloro-2-quinolinone

Solvents

chlorobenzene

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was cooled down
2. 2
   OtherThe product crystallized out as a pink solid which
3. 3
   Filtrationwas filtered
4. 4
   Otherdried

Procedure

To a mixture of N-(4-chlorophenyl)cinnamamide (8.3 g), and chlorobenzene (60 ml) was added portionwise aluminum chloride (21.4 g) under nitrogen at room temperature and the reaction mixture was slowly warmed up to 125° C. and kept at that temperature for 3 hours. The reaction mixture was cooled down and poured over 400 g of ice. The product crystallized out as a pink solid which was filtered and dried.

Source