2-(Phenylamino)benzonitrile → Ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylate

HRID 377619

反応式

HRID 377619 の反応式
[O-]CC.[Na+].C(O)C.[Na].[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([O-:13])=O.[C:18]1([NH:24][C:25]2[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=2[C:27]#[N:28])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(O)C>[NH2:28][C:27]1[C:26]2[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:11](=[O:13])[C:10]=1[C:9]([O:15][CH2:16][CH3:17])=[O:14]

参加物

6

反応物 4

HCID 2528802-(Phenylamino)benzonitrileHCID 3595298Propanedioic acid, monoethyl esterHCID 5360545SodiumHCID 23706232Ethanol sodium ethoxide

生成物 1

HCID 19356221Ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylate収率 51.7%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Into a sodium ethoxide/ethanol solution which had been prepared from 2.07 g (90 mmol) of metallic sodium and 75 ml of anhydrous ethanol, 14.4 g (90 mmol) of ethyl malonate were added dropwise at room temperature. After the resultant mixture was stirred for 30 minutes as was, 5.82 g (30 mmol) of 2-phenylaminobenzonitrile were added and the mixture so obtained was heated under reflux for 48 hours. The reaction mixture was concentrated under reduced pressure, followed by the addition of ethyl acetate. The resulting solution was washed with water and was then dried. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column and was then recrystallized from chloroform/hexane, whereby 4.78 g of ethyl 4-amino-2-oxo-1-phenyl-1,2-dihydro-quinoline-3-carboxylate (Compound No. 1) were obtained (yield: 51.7%).

後処理

  1. additionwere added dropwise at room temperature
  2. customthe mixture so obtained
  3. temperaturewas heated
  4. temperatureunder reflux for 48 hours
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. additionfollowed by the addition of ethyl acetate
  7. washThe resulting solution was washed with water
  8. customwas then dried
  9. distillationThe solvent was distilled off under reduced pressure
  10. customThe residue was purified by chromatography on a silica gel column
  11. customwas then recrystallized from chloroform/hexane

出典と根拠

ORDレコード
ord-032e1a16f50b49e68f874f7e59ca4e90
出典データセット
uspto-grants-2000_02
特許番号
US06028081

関連ノート

読み込み中…