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

HRID 1588960Notes

Reaction equation

HRID 1588960 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-].[Mg+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 5360315Magnesium Chloride

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 82.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Into 15 ml of dimethylformamide were dissolved with heating 1.37 g (0.01 mol) of anthranilic acid and 3.2 g of magnesium chloride (anhydrous), and the resulting solution was cooled to room temperature. 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 above solution, with stirring at room temperature. After the completion of the dropping, the reaction mixture was stirred for additional 1.5 hours, and then treated in the same manner as in Example 2. There was obtained 2.71 g (yield: 82.9%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid. Melting point: 209°-211° C.

Workup

  1. stirringAfter being stirred for additional 15 minutes
  2. additionthe resulting mixture was added dropwise to the above solution
  3. stirringwith stirring at room temperature
  4. stirringAfter the completion of the dropping, the reaction mixture was stirred for additional 1.5 hours
  5. additiontreated in the same manner as in Example 2

Sources & evidence

ORD record
ord-7b9d8ae3920e4c009a53d6b29acc8ddb
Source dataset
uspto-grants-1993_06
Patent number
US05223639

Reaction notes

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