Hydrochloric Acid → HCID 66596895, compound

HRID 1811389Notes

Reaction equation

HRID 1811389 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][CH2:19][C:20]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]2[C:21]=1[CH:22]=[CH:23][C:24](=[O:33])[N:25]2[CH3:32].Cl>ClCCl.C1COCC1>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:20]([CH2:19][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:21]2[C:26]=1[N:25]([CH3:32])[C:24](=[O:33])[CH:23]=[CH:22]2

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 24758Sodium hydrideHCID 66603271HCID 66603271, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66596895HCID 66596895, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil) (0.39 g) was added under ice cooling to a THF solution (30 ml) of diethyl malonate (1.85 ml), and stirring was carried out until the generation of hydrogen stopped. 5-(3-Iodopropyl)-8-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline (2.89 g) was added, followed by stirring at room temperature for 4.5 hours. 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=20:1). The purified product was concentrated under reduced pressure to thereby obtain 2.94 g (yield: 93%) of diethyl 2-[3-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)propyl]malonate as a yellow oil.

Workup

  1. stirringby stirring at room temperature for 4.5 hours
  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=20:1)
  5. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-491b333abd33405c9b8ffe79ab3cc3db
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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