Methyl Anthranilate → N-(3′,4′-Dimethoxycinnamoyl)anthranilic acid

HRID 1579043Notes

Reaction equation

HRID 1579043 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 63.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3bc097cbb3964bb4a5b5fd932e29f708
Source dataset
uspto-grants-1976_02
Patent number
US03940422

Reaction notes

Loading…