Pyridine → 4-Hydroxy-3-(4-trifluoromethoxy-benzoylamino)-benzoic acid

HRID 2196477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196477
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[OH:11])[C:5]([OH:7])=[O:6].N1C=CC=CC=1.[F:18][C:19]([F:31])([F:30])[O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1>C1COCC1>[OH:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=1[NH:1][C:25](=[O:26])[C:24]1[CH:28]=[CH:29][C:21]([O:20][C:19]([F:18])([F:30])[F:31])=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 650833-Amino-4-hydroxybenzoic acidHCID 1421104-(Trifluoromethoxy)benzoyl Chloride

Produkt 1

HCID 600571974-Hydroxy-3-(4-trifluoromethoxy-benzoylamino)-benzoic acidAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 3-Amino-4-hydroxy benzoic acid (0.136, 0.00089 mols) and pyridine (0.211 g, 0.00267 mols) in 13 ml dry THF is added 4-trifluoromethoxybenzoyl chloride (0.2 g, 0.00089 mols) and the solution is stirred under nitrogen atmosphere at RT for 10 hrs and then refluxed for 3 hrs. The reaction mixture is rotary evaporated and the residue is slurried in water and filtered to get the amide (0.175 g) which is taken for the next step without further purification.

Aufarbeitung

  1. temperaturerefluxed for 3 hrs
  2. customThe reaction mixture is rotary evaporated
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-fbdc46b66c6c49b59e96d9d0f5c776ff
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338459B2

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