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

HRID 902876ノート

反応式

HRID 902876 の反応式
[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]

参加物

4

反応物 2

HCID 78124-ChloroanilineHCID 12980Dimethyl acetylenedicarboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
240 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9d2bc446a18449daa2d9e34b5287be5d
出典データセット
uspto-grants-2008_04
特許番号
US07365205B2

反応ノート

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