Hydrochloric Acid → Ethyl 1,4-dihydro-3,6-dimethyl-4-oxoquinoline-2-carboxylate

HRID 1604543

Reaction equation

HRID 1604543 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[CH3:9][CH:10]([C:16](=O)[C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:11](OCC)=[O:12].Cl>ClCCl>[CH3:9][C:10]1[C:11](=[O:12])[C:7]2[C:2](=[CH:3][CH:4]=[C:5]([CH3:8])[CH:6]=2)[NH:1][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7813p-ToluidineHCID 97750Butanedioic acid, 2-methyl-3-oxo-, 1,4-diethyl ester

Product 1

HCID 19603453Ethyl 1,4-dihydro-3,6-dimethyl-4-oxoquinoline-2-carboxylateYield 71.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of p-toluidine (10 g) and diethyl 2-methyl-3-oxosuccinate (18.9 g) in dichloromethane (50 ml) was refluxed for 2 days. The reaction mixture was poured onto 0.5N hydrochloric acid (200 ml) and extracted with dichloromethane. The organic layer was washed with water, 0.5N sodium hydroxide solution and brine, dried over magnesium sulfate, and concentrated. The obtained residue was added to heated diphenyl (80 g) and the mixture was refluxed for 15 minutes. The reaction mixture was allowed to stand at ambient temperature, and the resulting precipitates were collected by filtration to give ethyl 1,4-dihydro-3,6-dimethyl-4-oxoquinoline-2-carboxylate (16.3 g).

Workup

  1. temperaturewas refluxed for 2 days
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water, 0.5N sodium hydroxide solution and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. additionThe obtained residue was added
  7. temperatureto heated diphenyl (80 g)
  8. temperaturethe mixture was refluxed for 15 minutes
  9. customto stand at ambient temperature
  10. customthe resulting precipitates
  11. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-35035b652c7b4b9a8d269d001da2f8d7
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Linked notes

Loading…