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

HRID 133140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133140
[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-amino-nicotinic 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-1ead4f7153614b019a4f77205513c9cd
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390815B2

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