4-Aminobenzoic Acid → 4-(4'-Acetoxycinnamoylamino)-benzoic acid

HRID 1904162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904162
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[C:11]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21](Cl)=[O:22])=[CH:17][CH:16]=1)(=[O:13])[CH3:12]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:11]([O:14][C:15]1[CH:25]=[CH:24][C:18]([CH:19]=[CH:20][C:21]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=2)=[O:22])=[CH:17][CH:16]=1)(=[O:13])[CH3:12]

Komponenten

5

Edukt 2

HCID 9784-Aminobenzoic AcidHCID 5903202-Propenoyl chloride, 3-[4-(acetyloxy)phenyl]-, (E)-

Produkt 1

HCID 536944204-(4'-Acetoxycinnamoylamino)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1049PyridineLösungsmittelHCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

In a mixture of 20 ml of dry chloroform and 10 ml of dry pyridine were dissolved 2.6 g of 4-aminobenzoic acid. To this mixture were added dropwise under cooling 20 ml of dry chloroform containing 3.2 g of 4-acetoxycinnamoyl chloride. The mixture was heated under reflux for 2 hours and the reaction mixture was concentrated under reduced pressure. The residue was poured into water and hydrochloric acid was then added to make the liquid weakly acidic. The precipitated crystals were collected by filtration and recrystallized from alcohol to yield 2.9 g of 4-(4'-acetoxycinnamoylamino)-benzoic acid. M.P.=305°-307° C. (with decomposition).

Aufarbeitung

  1. additionTo this mixture were added dropwise
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 2 hours
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. additionThe residue was poured into water and hydrochloric acid
  6. additionwas then added
  7. filtrationThe precipitated crystals were collected by filtration
  8. customrecrystallized from alcohol

Quellen und Nachweise

ORD-Eintrag
ord-6b99cc2322eb45179c6edbd40ddc75d3
Quelldatensatz
uspto-grants-1989_06
Patentnummer
USRE032944

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