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

HRID 1588963Notes

Reaction equation

HRID 1588963 reaction equation
CN(C)C=O.[C:6]([OH:15])(=[O:14])[C:7]1[C:8](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH2:9].S(Cl)(Cl)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:30](O)=[O:31])=[CH:24][C:23]=1[O:33][CH3:34]>O>[CH3:34][O:33][C:23]1[CH:24]=[C:25]([CH:26]=[CH:27][C:22]=1[O:21][CH3:20])[CH:28]=[CH:29][C:30]([NH:9][C:8]1[C:7](=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]([OH:15])=[O:14])=[O:31]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 6228Dimethylformamide2×HCID 24386Thionyl ChlorideHCID 717531(E)-3,4-Dimethoxycinnamic acid

Product 1

HCID 5527N-(3′,4′-Dimethoxycinnamoyl)anthranilic acidYield 38.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 15 ml of dimethylformamide was dissolved 2.06 g (0.015 mol) of anthranilic acid. 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, 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 1. There was obtained 1.26 g (yield: 38.5%) of N-(3',4'-dimethoxycinnamoyl)-anthranilic acid.

Workup

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

Sources & evidence

ORD record
ord-b286f784b2fd4e4bbbefea100b93a655
Source dataset
uspto-grants-1993_06
Patent number
US05223639

Reaction notes

Loading…