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

HRID 133140Notes

Reaction equation

HRID 133140 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-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.

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-1ead4f7153614b019a4f77205513c9cd
Source dataset
uspto-grants-2008_06
Patent number
US07390815B2

Reaction notes

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