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

HRID 454184ノート

反応式

HRID 454184 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 296364Ethyl 4-hydroxy-7-methoxyquinoline-3-carboxylate収率 45%

試薬・触媒・溶媒 1

HCID 7583Diphenyl Ether溶媒

反応条件

温度
240 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-48122447182f416f976410885abcdf8e
出典データセット
uspto-grants-2013_07
特許番号
US08492560B2

反応ノート

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