Dimethylformamide → 1-(4-Chlorobenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde

HRID 1811397Notes

Reaction equation

HRID 1811397 reaction equation
[H-].[Na+].CN(C=O)C.[O:8]=[C:9]1[C:18]([CH:19]=[O:20])=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10]1.[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Br)=[CH:24][CH:23]=1>C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][N:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:17]=[C:18]([CH:19]=[O:20])[C:9]2=[O:8])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 5893342-Hydroxyquinoline-3-carbaldehyde

Product 1

HCID 866139161-(4-Chlorobenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxaldehydeYield 74.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60% in oil) (1.3 g) was added at 0° C. to a DMF solution (50 ml) of 2-oxo-1,2-dihydroquinoline-3-carboxaldehyde (5.13 g), followed by stirring for 30 minutes. 4-chlorobenzyl bromide (7.0 g) was added, and the resulting mixture was stirred at room temperature overnight. Water was added to the reaction mixture, extraction with ethyl acetate was performed, and the extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:4). The purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent to thereby obtain 6.57 g (yield: 72%) of 1-(4-chlorobenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxaldehyde as a white powder.

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. dry with materialthe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:10→1:4)
  5. customThe purified product was recrystallized from a chloroform-diisopropyl ether mixed solvent

Sources & evidence

ORD record
ord-6be90d041f454d9197f276171979e49a
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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