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

HRID 2104403Notes

Reaction equation

HRID 2104403 reaction equation
[C:1]([C:7]([O:9]C)=O)#[C:2][C:3]([O:5][CH3:6])=[O:4].[Cl:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1>CO>[CH3:6][O:5][C:3]([C:2]1[NH:16][C:15]2[C:17]([C:7](=[O:9])[CH:1]=1)=[CH:18][C:12]([Cl:11])=[CH:13][CH:14]=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 thus-obtained mixture was heated under reflux for 8 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in diphenyl ether (70 mL), followed by stirring at 240° C. for 4 hours. After the reaction mixture was cooled, a solvent mixture of hexane and diethyl ether was added thereto. The precipitated crystals were collected by filtration, and were washed, to thereby give the title compound (11.09 g).

Workup

  1. temperaturethe thus-obtained 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. temperatureAfter the reaction mixture was cooled
  6. additiona solvent mixture of hexane and diethyl ether
  7. additionwas added
  8. filtrationThe precipitated crystals were collected by filtration
  9. washwere washed

Sources & evidence

ORD record
ord-d13ae911c67b4659a644aa86061d5db5
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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