1-Pentanol → 2-[(4-Methoxyphenyl)amino]benzoic acid

HRID 1439206

Reaktionsgleichung

Reaktionsgleichung von HRID 1439206
Cl[C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCCC>[Cu]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

Komponenten

6

Edukt 4

HCID 62761-PentanolHCID 7732P-AnisidineHCID 83742-Chlorobenzoic AcidHCID 11430Potassium Carbonate

Produkt 1

HCID 2029182-[(4-Methoxyphenyl)amino]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

A mixture of 80 g. 2-chlorobenzoic acid, 80 g. 4-anisidine, 80 g. potassium carbonate, 4 g. activated copper powder, and 800 ml. amyl alcohol was heated under reflux with efficient stirring for 4 hours. The amyl alcohol was removed by steam distillation and the remaining aqueous phase was filtered and made neutral by addition of 1:1 concentrated hydrochloric acid-water. The resulting solid (102 g.) was collected by filtration to give after recrystallization from isopropyl alcohol N-(4-methoxyphenyl)anthranilic acid; m.p. 183°-184° C.

Aufarbeitung

  1. additionA mixture of 80 g
  2. temperatureunder reflux
  3. customThe amyl alcohol was removed by steam distillation
  4. filtrationthe remaining aqueous phase was filtered
  5. additionmade neutral by addition of 1:1 concentrated hydrochloric acid-water
  6. filtrationThe resulting solid (102 g.) was collected by filtration
  7. customto give
  8. customafter recrystallization from isopropyl alcohol N-(4-methoxyphenyl)anthranilic acid

Quellen und Nachweise

ORD-Eintrag
ord-03d0e6779745477c814cfade4e9828fc
Quelldatensatz
uspto-grants-1977_11
Patentnummer
US04058532

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