Methyl Anthranilate → N-(3',4'-dimethoxycinnamoyl)anthranilic acid

HRID 1579043ノート

反応式

HRID 1579043 の反応式
O1CCOCC1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([OH:16])=O.P(Cl)(Cl)(Cl)=O.[C:27]([O:36]C)(=[O:35])[C:28]1[C:29](=[CH:31][CH:32]=[CH:33][CH:34]=1)[NH2:30]>N1C=CC=CC=1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[CH:12]=[CH:13][C:14]([NH:30][C:29]1[C:28](=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:27]([OH:36])=[O:35])=[O:16]

参加物

6

反応物 4

HCID 8635Methyl AnthranilateHCID 168483',4'-Dimethoxycinnamic acidHCID 24813Phosphorus oxychlorideHCID 312751,4-Dioxane

生成物 1

HCID 5527N-(3',4'-dimethoxycinnamoyl)anthranilic acid収率 63.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

To a mixture of 20 ml of dry dioxane and 0.7 g of dry pyridine were added 2 g of 3,4-dimethoxycinnamic acid, 1.6 g of phosphorus oxychloride and 1.6 g of methyl anthranilate. The mixture was heated under reflux for 2 hours to effect reaction. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved with heating in ethanol and then cooled whereby crystals were precipitated. The crystals were separated by filtration and treated in a manner similar to that described in Example 5 to effect hydrolysis of the ester group. The product was recrystallized from chloroform to obtain 2 g of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid having a melting point of 211°-213°C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customreaction
  4. customAfter completion of the reaction
  5. concentrationthe reaction mixture was concentrated
  6. dissolutionthe residue was dissolved
  7. temperaturewith heating in ethanol
  8. temperaturecooled whereby crystals
  9. customwere precipitated
  10. customThe crystals were separated by filtration
  11. additiontreated in a manner similar to
  12. customhydrolysis of the ester group
  13. customThe product was recrystallized from chloroform

出典と根拠

ORDレコード
ord-3bc097cbb3964bb4a5b5fd932e29f708
出典データセット
uspto-grants-1976_02
特許番号
US03940422

反応ノート

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