Diethyl (ethoxymethylene)malonate → Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate

HRID 454184노트

반응식

HRID 454184 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.C([O:12][CH:13]=[C:14]([C:20](OCC)=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16])C.C(C1C=NC2C(C=1)=CC=C(OC1C3C(=CC(OCC4CCN(C)CC4)=C(OC)C=3)N=CN=1)C=2)#N>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:6]([C:13](=[O:12])[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:20][NH:9]2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 6871Diethyl (ethoxymethylene)malonateHCID 108243-MethoxyanilineHCID 220305324-(3-Cyanoquinolin-7-yloxy)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazoline

생성물 1

HCID 296364Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate수율 45%

시약·촉매·용매 1

HCID 7583Diphenyl Ether용매

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온도
240 °C

실험 절차

m-Anisidine (50 g, 407 mmol) and diethyl ethoxymethylenemalonate (102 g, 407 mmol) were heated at 60° C. for 20 minutes. Diphenyl ether (270 ml) was then added and the temperature was raised to 240° C. over 30 minutes. The ethanol formed distilled off. Heating was maintained at this temperature for 1 hour then the reaction mixture was allowed to cool to 120° C. at which point the reaction mixture was diluted with heptane and allowed to stand overnight at ambient temperature. The brown solid was collected by filtration and washed with methanol and ether to give ethyl 7-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (45 g, 45%). This reaction was repeated twice.

후처리

  1. distillationdistilled off
  2. temperatureHeating
  3. temperaturewas maintained at this temperature for 1 hour
  4. temperatureto cool to 120° C. at which
  5. additionwas diluted with heptane
  6. filtrationThe brown solid was collected by filtration
  7. washwashed with methanol and ether

출처 및 근거

ORD 기록
ord-48122447182f416f976410885abcdf8e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492560B2

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