Hydrochloric Acid → HCID 66597041, compound

HRID 503975Notes

Reaction equation

HRID 503975 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-6c1cc9b1136142289e1af82c54468d9d
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

Loading…