4-Pyridinecarboxylic acid, 1-oxide → N-[4-chloro-3-(trifluoromethyl)phenyl]-4-pyridinecarboxamide-1-oxide

HRID 568404

Reaction equation

HRID 568404 reaction equation
[C:1]([OH:10])(=O)[C:2]1[CH:7]=[CH:6][N+:5]([O-:8])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH2:30])=[CH:26][C:25]=1[C:31]([F:34])([F:33])[F:32]>CN(C)C=O>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([NH:30][C:1]([C:2]2[CH:3]=[CH:4][N+:5]([O-:8])=[CH:6][CH:7]=2)=[O:10])=[CH:26][C:25]=1[C:31]([F:32])([F:33])[F:34]

Participants

5

Reactant 3

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 13604808N-[4-chloro-3-(trifluoromethyl)phenyl]-4-pyridinecarboxamide-1-oxideYield 56.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of isonicotinic acid 1-oxide (4.16 g, 29.9 mmol) and 1,1'-Carbonyldiimidazole (5.33 g, 32.9 mmol) in dry dimethylformamide (50 ml) was stirred for 40 minutes under an air-lock and treated with 4-chloro-3-trifluoromethylbenzenamine (6.43 g, 32.9 mmol). The reaction mixture was heated at 100° for 5.3 hours and cooled to room temperature. The solution was evaporated in vacuo and the residue triturated with ethanol (2×20 ml) to give the title compound (5.379 g), m.p. 263°-265°.

Workup

  1. temperatureThe reaction mixture was heated at 100° for 5.3 hours
  2. customThe solution was evaporated in vacuo
  3. customthe residue triturated with ethanol (2×20 ml)

Sources & evidence

ORD record
ord-54cd37725b2e4478be3ec63150bef675
Source dataset
uspto-grants-1988_03
Patent number
US04728658

Linked notes

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