Hydrochloric Acid → HCID 66596952, compound

HRID 1811386Notes

Reaction equation

HRID 1811386 reaction equation
[H-].[Na+].[C:3]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[H][H].I[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23](=[O:32])[N:24]2[CH3:31].Cl>ClCCl.O1CCCC1>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:19]([CH2:18][CH2:17][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[C:3]([O:11][CH2:12][CH3:13])=[O:10])=[C:20]2[C:25]=1[N:24]([CH3:31])[C:23](=[O:32])[CH:22]=[CH:21]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 66596887HCID 66596887, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66596952HCID 66596952, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil) (0.5 g) was added under ice cooling to a tetrahydrofuran (THF) solution (30 ml) of diethyl malonate (2.2 ml), and stirring was carried out until the generation of hydrogen stopped. 5-(2-iodoethyl)-8-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline (1.54 g) was added, followed by stirring at room temperature overnight. The reaction mixture was added to cold hydrochloric acid, and extraction with dichloromethane was performed. After drying over anhydrous sodium sulfate, the dry product was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1→40:1). The purified product was under reduced pressure to thereby obtain 1.73 g (yield: quantitative) of diethyl 2-[2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]malonate as a yellow oil.

Workup

  1. stirringby stirring at room temperature overnight
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe dry product was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=50:1→40:1)

Sources & evidence

ORD record
ord-3f2ec98d2dff455e8d804040e2fdd5a7
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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