Anthranilic Acid → N-(3',4'-dimethoxycinnamoyl)anthranilic acid

HRID 1588960Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588960
[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]

Komponenten

7

Edukt 4

HCID 227Anthranilic AcidHCID 24386Thionyl ChlorideHCID 7175313,4-Dimethoxycinnamic acidHCID 5360315Magnesium Chloride

Produkt 1

HCID 5527N-(3',4'-dimethoxycinnamoyl)anthranilic acidAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-7b9d8ae3920e4c009a53d6b29acc8ddb
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223639

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