Water → 2-(2-Trifluoromethyl-phenyl)-pyrido[2,3-d][1,3]oxazin-4-one

HRID 38171

Reaktionsgleichung

Reaktionsgleichung von HRID 38171
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[NH2:14][C:15]1[N:23]=[CH:22][CH:21]=[CH:20][C:16]=1[C:17](O)=[O:18].O>N1C=CC=CC=1>[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]1[O:6][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][CH:22]=[N:23][C:15]=2[N:14]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 675612-(Trifluoromethyl)benzoyl chlorideHCID 729302-Aminonicotinic acid

Produkt 1

HCID 219391472-(2-Trifluoromethyl-phenyl)-pyrido[2,3-d][1,3]oxazin-4-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

2-(Trifluoromethyl)benzoyl chloride (4.2 ml, 29.2 mmol) is added dropwise to a solution of 2-aminonicotinic acid (2.04 g, 14.76 mmol) in 20 ml of pyridine. The reaction mixture is heated at 158 C for 30 min then cooled to room temperature. The reaction is poured into 200 ml of water and an oil forms which solidifies upon stirring. The solid is collected by vacuum filtration and washed with water and diethyl ether. The product is dried to give 2-(2-trifluoromethyl-phenyl)-pyrido[2,3-d][1,3]oxazin-4-one (2.56 g, 60% yield) which may be used in the next step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at 158 C for 30 min
  2. filtrationThe solid is collected by vacuum filtration
  3. washwashed with water and diethyl ether
  4. customThe product is dried

Quellen und Nachweise

ORD-Eintrag
ord-22c0a15041374cc09a71555f34042458
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524720B2

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