Dimethylformamide → 1-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 504011Notes

Reaction equation

HRID 504011 reaction equation
[H-].[Na+].CN(C=O)C.[CH3:8][O:9][C:10]1[C:19]2[NH:18][C:17](=[O:20])[CH2:16][CH2:15][C:14]=2[C:13]([CH:21]=[O:22])=[CH:12][CH:11]=1.[CH3:23][O:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)=[O:26]>C(OCC)(=O)C.O>[C:25]([C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:18]2[C:19]3[C:10]([O:9][CH3:8])=[CH:11][CH:12]=[C:13]([CH:21]=[O:22])[C:14]=3[CH2:15][CH2:16][C:17]2=[O:20])=[CH:29][CH:28]=1)([O:24][CH3:23])=[O:26]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoateHCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

Product 1

HCID 866139251-(4-Carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeYield 62.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil) (2.87 g) was added at 0° C. to a DMF solution (100 ml) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (13.4 g), followed by stirring for 30 minutes. Methyl 4-bromomethyl benzoate (18.0 g) was added, and the resulting mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was washed with a saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4→1:2). The purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent to thereby obtain 14.43 g (yield: 62%) of 1-(4-carbomethoxybenzyl)-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a white powder.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. washThe extract was washed with a saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:4→1:2)
  6. customThe purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent

Sources & evidence

ORD record
ord-ab9498d3839c41a79fd0d3412c656a01
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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