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

HRID 1392770노트

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HRID 1392770 반응식
[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]

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 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).

후처리

  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

출처 및 근거

ORD 기록
ord-f07b1626d2554b2ead3bf661e5387cb4
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342014B2

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