Anthranilic Acid → N-(3′,4′-Dimethoxycinnamoyl)anthranilic acid

HRID 1588962Notes

Reaction equation

HRID 1588962 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].S(Cl)(Cl)=O.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:23]=[CH:24]/[C:25](O)=[O:26])=[CH:19][C:18]=1[O:28][CH3:29]>O.CN(C)C=O.N1C=CC=CC=1>[CH3:29][O:28][C:18]1[CH:19]=[C:20]([CH:21]=[CH:22][C:17]=1[O:16][CH3:15])[CH:23]=[CH:24][C:25]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])=[O:26]

Participants

7

Reactant 3

HCID 227Anthranilic AcidHCID 24386Thionyl ChlorideHCID 717531(E)-3,4-Dimethoxycinnamic acid

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 40.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1049PyridineSolventHCID 6228DimethylformamideSolvent2×

Procedure

Into 15 ml of dimethylformamide were dissolved 1.51 g (0.011 mol) of anthranilic acid and 1.6 g of pyridine. To 10 ml of dimethylformamide were added in order 0.78 ml of thionyl chloride and 2.08 g (0.01 mol) of 3',4'-dimethoxycinnamic acid, during which the reaction system was stirred and cooled with ice and water. The resulting mixture was added dropwise to the above solution, during which the reaction system was stirred and cooled with ice and water. After the completion of the dropping, the reaction mixture was stirred for 30 minutes at the same temperature and then for 1 hour at room temperature. After the completion of the reaction, 80 ml of ice-water mixture was added thereto. The, air was introduced thereinto for 30 minutes, and crystals deposited were collected by filtration and recrystallized from chloroform to give 1.33 g (yield: 40.7%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid.

Workup

  1. additionThe resulting mixture was added dropwise to the above solution, during which the reaction system
  2. stirringwas stirred
  3. stirringAfter the completion of the dropping, the reaction mixture was stirred for 30 minutes at the same temperature
  4. additionwas added
  5. additionThe, air was introduced
  6. waitfor 30 minutes
  7. filtrationcrystals deposited were collected by filtration
  8. customrecrystallized from chloroform

Sources & evidence

ORD record
ord-fa722bd50c15426097d862a7465be19c
Source dataset
uspto-grants-1993_06
Patent number
US05223639

Reaction notes

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