Anthranilic Acid → HCID 19757772, Verbindung

HRID 1587416Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1587416
Cl[CH2:2][C:3]([NH:5][C:6]1[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:8]([OH:10])=[O:9])=[O:4].[C:15](O)(=O)[C:16]1[C:17](=[CH:19][CH:20]=[CH:21][CH:22]=1)N.NC1C=CC=C(C)C=1>CN(C)C=O>[CH3:15][C:16]1[CH:22]=[C:21]([CH2:2][C:3]([NH:5][C:6]2[C:7](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:8]([OH:10])=[O:9])=[O:4])[CH:20]=[CH:19][CH:17]=1

Komponenten

5

Edukt 3

HCID 227Anthranilic AcidHCID 7934m-ToluidineHCID 919916HCID 919916, Verbindung

Produkt 1

HCID 19757772HCID 19757772, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N(chloroacetyl)anthranilic acid 6.4 g (15 mmol) (synthesized from anthranilic acid by the same procedures as those of Example 9) and m-toluidine 9.5 ml (0.09 mol) were dissolved in 60 ml of dimethylformamide and heated at 80° to 90° C. for 4 hours. The reaction mixture was poured into ice water and extracted with ether. The resulting ether solution was extracted with 10% sodium hydroxide and the resulting aqueous solution was neutralized with 10% HCl solution. The neutralized solution was extracted with ether, and the ether solution was washed with water and dried. The solvent of dried solution was distilled off and the residue was recrystallized from benzene-hexane to obtain N[(3-methylphenyl)acetyl]anthranilic acid 4.7 g (yield: 57%).

Aufarbeitung

  1. temperatureheated at 80° to 90° C. for 4 hours
  2. extractionextracted with ether
  3. extractionThe resulting ether solution was extracted with 10% sodium hydroxide
  4. extractionThe neutralized solution was extracted with ether
  5. washthe ether solution was washed with water
  6. customdried
  7. distillationThe solvent of dried solution was distilled off
  8. customthe residue was recrystallized from benzene-hexane

Quellen und Nachweise

ORD-Eintrag
ord-271598d7d86e43dfb17a0df6c582f175
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05217961

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