Carbon Dioxide → Methyl 1,4-dihydro-7-methoxy-4-oxo-6-quinolinecarboxylate

HRID 393664

反応式

HRID 393664 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22])[NH:6][CH:7]=[C:8]1[C:13](=[O:14])OC(C)(C)OC1=O.C(=O)=O>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:18]([C:13](=[O:14])[CH:8]=[CH:7][NH:6]2)=[CH:19][C:20]=1[C:21]([O:23][CH3:24])=[O:22]

参加物

4

反応物 2

HCID 280Carbon DioxideHCID 22646557Methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)amino)-2-methoxybenzoate

生成物 1

HCID 22646623Methyl 1,4-dihydro-7-methoxy-4-oxo-6-quinolinecarboxylate収率 80%

試薬・触媒・溶媒 1

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

反応条件

温度
185 °C

実験手順

5-((3-Methoxy-4-methoxycarbonylanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (10 g, 29.8 mmol) was suspended in DOWTHERM A, (trade mark of Fluka Chemie AG), (125 ml) and heated to 180-190° C. over 30 minutes. The starting material dissolved at 100° C. and carbon dioxide came off at approximately 180° C. The heating was stopped after a further 30 minutes and the product precipitated out as the temperature dropped. Upon reaching 40° C. ether was added and the mixture was stirred for 30 minutes. The solid was collected by filtration, washed with ether and dried under vacuum to give 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.56 g, 80%).

後処理

  1. dissolutionThe starting material dissolved at 100° C.
  2. customcame off at approximately 180° C
  3. customthe product precipitated out as the temperature
  4. additiondropped
  5. customUpon reaching 40° C.
  6. additionwas added
  7. filtrationThe solid was collected by filtration
  8. washwashed with ether
  9. customdried under vacuum

出典と根拠

ORDレコード
ord-241da655c37841408a9984bf1f2e178f
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

関連ノート

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