Hydrochloric Acid → HCID 66597041, compound

HRID 1811384Notes

Reaction equation

HRID 1811384 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:17][CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:9]2[C:14]=1[N:13]([CH3:15])[C:12](=[O:16])[CH:11]=[CH:10]2.[H][H].[Cl:31]N1C(=O)CCC1=O.Cl>ClCCl.O1CCCC1>[Cl:31][C: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:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 31398ChlorosuccinimideHCID 66596974HCID 66596974, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 66597041HCID 66597041, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil) (1.0 g) was added under ice cooling to a tetrahydrofuran (THF) solution (140 ml) of 13.59 g of diethyl 2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)malonate, and stirring was carried out until the generation of hydrogen stopped. N-chlorosuccinimide (5.6 g) was added, followed by stirring for 1 hour. 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, diisopropyl ether was added to the residue, and the precipitated solid was collected by filtration and dried to thereby obtain 12.77 g (yield: 86%) of diethyl 2-chloro-2-(8-methoxy-1-methyl-2-oxo-1,2-dihydroquinolin-5-ylmethyl)malonate as a light yellow powder.

Workup

  1. stirringby stirring for 1 hour
  2. dry with materialAfter drying over anhydrous sodium sulfate
  3. concentrationthe dry product was concentrated under reduced pressure, diisopropyl ether
  4. additionwas added to the residue
  5. filtrationthe precipitated solid was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-ba26afc69da4455381508fe3f2da9e9b
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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