Dimethylformamide → HCID 86613916, compound

HRID 503988Notes

Reaction equation

HRID 503988 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 86613916HCID 86613916, compoundYield 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-9e7a01cee91b48e1bf118eee2345eedd
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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