Chloroacetyl chloride → 1-(Chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

1.78 g of 7-nitro-1,2,3,4-tetrahydroquinoline (0.01 mol) are dissolved in 15 ml of ethyl acetate. This solution is run into a mixture of 15 ml of ethyl acetate and 0.80 ml of chloroacetyl chloride. A white precipitate forms immediately, and stirring is continued at 30° C. for 2 h (the reaction is monitored by thin layer chromatography (90/10 ethyl acetate/heptane)). After 2 h, since the reaction is incomplete, 0.2 equivalent of chloroacetyl chloride is added and the temperature is raised to 60° C.; the solid formed undergoes dissolution. When the reaction has finished, the mixture is cooled and the solvent is evaporated off. 2.46 g of a beige product which corresponds to the expected compound are recovered.

Provenance & Evidence