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

HRID 2121455Notes

Reaction equation

HRID 2121455 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-165b1d50d01e4515be29420c6122dcd3
Source dataset
uspto-grants-2004_02
Patent number
US06696452B2

Reaction notes

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