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

HRID 377619

반응식

HRID 377619 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-032e1a16f50b49e68f874f7e59ca4e90
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06028081

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