m-Toluidine → Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 430554

반응식

HRID 430554 반응식
C(O[CH2:4][CH:5]([C:11]([O:13]CC)=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[CH:18]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[OH:13][C:11]1[C:22]2[C:17](=[CH:18][C:19]([CH3:23])=[CH:20][CH:21]=2)[N:16]=[CH:4][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

참가 물질

4

반응물 2

HCID 7934m-ToluidineHCID 98702Diethyl (ethoxymethyl)malonate

생성물 1

HCID 178469524Ethyl 7-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylate수율 76.3%

시약·촉매·용매 1

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)용매

반응 조건

온도
100 °C

실험 절차

Diethyl ethoxymethylmalonate (37.8 mL, 187 mmol) and m-toluidine (20.0 mL, 187 mmol) were combined and heated at 100° C. for about 3 hours. The reaction mixture was allowed to cool to ambient temperature and it solidified. Dowtherm A (350 mL) was added and the reaction mixture was heated at reflux for about 30 minutes. The reaction mixture was allowed to cool to ambient temperature. The resulting precipitate was isolated by filtration, rinsed with acetone and dried to provide 33 g of ethyl 4-hydroxy-7-methyl-3-quinolinecarboxylate as a tan powder.

후처리

  1. temperatureto cool to ambient temperature
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for about 30 minutes
  4. temperatureto cool to ambient temperature
  5. customThe resulting precipitate was isolated by filtration
  6. washrinsed with acetone
  7. customdried

출처 및 근거

ORD 기록
ord-1ea39f341a784220968943198e07225e
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323200B1

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