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

HRID 11815

Reaktionsgleichung

Reaktionsgleichung von HRID 11815
[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-7f2377b602104b21a0f343502473fa9e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098330B2

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