Dimethylformamide → 1-Benzyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

HRID 504010Notes

Reaction equation

HRID 504010 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.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(OCC)(=O)C.O>[CH2:23]([N:18]1[C:19]2[C:10]([O:9][CH3:8])=[CH:11][CH:12]=[C:13]([CH:21]=[O:22])[C:14]=2[CH2:15][CH2:16][C:17]1=[O:20])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 859802658-Methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde

Product 1

HCID 866139241-Benzyl-8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehydeYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil) (1.07 g) was added at 0° C. to a DMF solution (50 ml) of 8-methoxy-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde (5.0 g), followed by stirring for 30 minutes. Benzyl bromide (3.47 ml) was added, and the resulting mixture was stirred at room temperature for 1 hour. 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 recrystallized from an ethyl acetate-n-hexane mixed solvent to thereby obtain 6.6 g (yield: 92%) of 1-benzyl-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 for 1 hour
  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 recrystallized from an ethyl acetate-n-hexane mixed solvent

Sources & evidence

ORD record
ord-d92cffd0ae69487ca0c507c12e0da34c
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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