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

HRID 844524Notes

Reaction equation

HRID 844524 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([OH:18])=[C:10]([C:19]([O:21]CC)=O)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:25]([NH:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].Cl>C(Cl)(Cl)Cl>[CH2:32]([N:31]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:19]([C:10]1[C:9](=[O:24])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:17]2[C:12]([C:11]=1[OH:18])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:21])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8920DihexylamineHCID 54711837Ethyl 1-benzyl-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate

Product 1

HCID 54688363N,N-dihexyl-1-benzyl-4-hydroxy-1,2-dihydro-2-oxoquinoline-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
130 °C

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.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction solution
  2. washthe separated organic phase was washed with 1 N hydrochloric acid and water
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. customAfter removal of the drying agent
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by chromatography ((silica gel; Merk silica gel 230-4000 mesh (Merk Co.), developing solvent; chloroform)
  8. customto stand for crystallization

Sources & evidence

ORD record
ord-8948a8785e2b454ea7e870262d0be038
Source dataset
uspto-grants-2002_04
Patent number
US06380384B1

Reaction notes

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