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

HRID 2104403노트

반응식

HRID 2104403 반응식
[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]

참가 물질

4

반응물 2

HCID 78124-ChloroanilineHCID 12980Dimethyl acetylenedicarboxylate

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
240 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d13ae911c67b4659a644aa86061d5db5
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07576135B2

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