Reaction #931706

Reaction equation

hydrochloric acid

ethyl 1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxylate

dihexylamine

→

N,N-dihexyl-1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxamide

Solvents

chloroform

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature, to the reaction solution
2. 2
   Washthe separated organic phase was washed with 1 N hydrochloric acid and water
3. 3
   DryingThe organic phase was dried over anhydrous magnesium sulfate
4. 4
   OtherAfter removal of the drying agent
5. 5
   Filtrationby filtration
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure
7. 7
   OtherThe residue was purified by chromatography ((silica gel; Merk silica gel 230-4000 mesh (Merk Co.), developing solvent; chloroform)
8. 8
   Otherto stand for crystallization

Procedure

A mixture of 0.30 g of ethyl 1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxylate and 2 ml of dihexylamine was stirred under heating at 130° C. for 2 hours. After cooling to room temperature, to the reaction solution were added chloroform and 1 N hydrochloric acid, and the separated organic phase was washed with 1 N hydrochloric acid and water. The organic phase was dried over anhydrous magnesium sulfate. After removal of the drying agent by filtration, the filtrate was concentrated under reduced pressure. The residue was purified by chromatography ((silica gel; Merk silica gel 230-4000 mesh (Merk Co.), developing solvent; chloroform) and allowed to stand for crystallization to give 0.36 g of N,N-dihexyl-1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxamide.

Source