4-Chloroaniline → methyl 6-chloro-4-oxo-1,4-dihydroquinoline-2-carboxylate

HRID 902876Notes

Reaction equation

HRID 902876 reaction equation
[C:1]([C:7]([O:9][CH3:10])=[O:8])#[C:2][C:3](OC)=[O:4].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>CO>[Cl:11][C:12]1[CH:13]=[C:14]2[C:15](=[CH:17][CH:18]=1)[NH:16][C:1]([C:7]([O:9][CH3:10])=[O:8])=[CH:2][C:3]2=[O:4]

Participants

4

Reactant 2

HCID 78124-ChloroanilineHCID 12980Dimethyl acetylenedicarboxylate

Product 1

HCID 5200373methyl 6-chloro-4-oxo-1,4-dihydroquinoline-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
240 °C

Procedure

Dimethyl acetylenedicarboxylate (13.5 ml) was added to a solution of 4-chloroaniline (12.76 g) in methanol (150 ml), and the mixture was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, the residue was dissolved in diphenyl ether (70 ml), and the solution was heated under reflux at 240° C. for 4 hours. After cooling the reaction mixture, a mixed solvent of hexane and diethyl ether was added, and crystals deposited were collected by filtration and washed to obtain the title compound (11.09 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 8 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe residue was dissolved in diphenyl ether (70 ml)
  5. temperaturethe solution was heated
  6. temperatureAfter cooling the reaction mixture
  7. additiona mixed solvent of hexane and diethyl ether was added
  8. filtrationcrystals deposited were collected by filtration
  9. washwashed

Sources & evidence

ORD record
ord-9d2bc446a18449daa2d9e34b5287be5d
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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