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

HRID 1588957Notes

Reaction equation

HRID 1588957 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[Cl-].[Ca+2].[Cl-].S(Cl)(Cl)=O.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](/[CH:26]=[CH:27]/[C:28](O)=[O:29])=[CH:22][C:21]=1[O:31][CH3:32]>O.CN(C)C=O>[CH3:32][O:31][C:21]1[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=1[O:19][CH3:18])[CH:26]=[CH:27][C:28]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])=[O:29]

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 24386Thionyl ChlorideHCID 717531(E)-3,4-Dimethoxycinnamic acidHCID 5284359Calcium Chloride

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 71.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

Into 15 ml of dimethylformamide were dissolved with heating 2.0 g of anthranilic acid and 2.3 g of anhydrous calcium chloride. To 10 ml of dimethylformamide were added in order 0.78 ml of thionyl chloride and 2.08 g 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. Then, air was introduced thereinto for 30 minutes, and crystals deposited were collected by filtration and recrystallized from ethanol-water (1:2) to give 2.35 g (yield: 71.8%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid. Melting point: 209°-211° C.

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. additionThen, air was introduced
  6. waitfor 30 minutes
  7. filtrationcrystals deposited were collected by filtration
  8. customrecrystallized from ethanol-water (1:2)

Sources & evidence

ORD record
ord-6675ad28a16f43ec9e2d6a2957038164
Source dataset
uspto-grants-1993_06
Patent number
US05223639

Reaction notes

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