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

HRID 1588958Notes

Reaction equation

HRID 1588958 reaction equation
[CH3:1][N:2](C)[CH:3]=[O:4].S(Cl)(Cl)=O.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/C(O)=O)=[CH:14][C:13]=1[O:23][CH3:24].[OH2:25]>>[CH3:24][O:23][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:12]=1[O:11][CH3:10])[CH:18]=[CH:19][C:3]([NH:2][C:1]1[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:12]([OH:11])=[O:25])=[O:4]

Participants

5

Reactant 4

HCID 962WaterHCID 6228Dimethylformamide2×HCID 24386Thionyl ChlorideHCID 717531(E)-3,4-Dimethoxycinnamic acid

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 78.9%

Procedure

Into 15 ml of dimethylformamide was dissolved with heating 4.65 g (0.02 mol) of anthranilic acid-magnesium chloride complex. 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. After being stirred for additional 15 minutes, the resulting mixture was added dropwise to the solution of anthranilic acid-magnesium chloride complex. 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 recystallized from ethanol-water (1:3) to give 2.58 g (78.9%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid. Molting point: 209°-211° C.

Workup

  1. temperaturewith heating 4.65 g (0.02 mol) of anthranilic acid-magnesium chloride complex
  2. stirringAfter being stirred for additional 15 minutes
  3. additionthe resulting mixture was added dropwise to the solution of anthranilic acid-magnesium chloride complex
  4. stirringAfter the completion of the dropping, the reaction mixture was stirred for 30 minutes at the same temperature
  5. additionwas added
  6. additionThen, air was introduced
  7. waitfor 30 minutes
  8. filtrationcrystals deposited were collected by filtration

Sources & evidence

ORD record
ord-058045ac6f2b4f1aad725be7aa59c46d
Source dataset
uspto-grants-1993_06
Patent number
US05223639

Reaction notes

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