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

HRID 2104403ノート

反応式

HRID 2104403 の反応式
[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]

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 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).

後処理

  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

出典と根拠

ORDレコード
ord-d13ae911c67b4659a644aa86061d5db5
出典データセット
uspto-grants-2009_08
特許番号
US07576135B2

反応ノート

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