Hydrochloric Acid → HCID 66596981, compound

HRID 503978Notes

Reaction equation

HRID 503978 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:17][CH2:18][CH:19]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]2[C:14]=1[N:13]([CH3:15])[C:12](=[O:16])[CH:11]=[CH:10]2.[H][H].[Cl:32]N1C(=O)CCC1=O.Cl>ClCCl.C1COCC1>[Cl:32][C:19]([CH2:18][CH2:17][C:8]1[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:16])[N:13]2[CH3:15])([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31398ChlorosuccinimideHCID 66596952HCID 66596952, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66596981HCID 66596981, compoundYield 121.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil) (0.21 g) was added under ice cooling to a THF solution (30 ml) of 1.79 g of diethyl 2-[2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]malonate, and stirring was carried out until the generation of hydrogen stopped. N-chlorosuccinimide (0.7 g) was added, followed by stirring for 1.5 hours. The reaction mixture was added to cold hydrochloric acid, and extraction with dichloromethane was performed. The extract was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain 2.38 g (yield: quantitative) of diethyl 2-chloro-2-[2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]malonate as a yellow oil.

Workup

  1. stirringby stirring for 1.5 hours
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efad44b9f1864978aba59fce6ca1255e
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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