3,4-Dichloroaniline → N-(3,4-dichlorophenyl)-4-pyridinecarboxamide-1-oxide

HRID 568403

Reaction equation

HRID 568403 reaction equation
[N+:1]1([O-:10])[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3][CH:2]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:23][C:24]1[CH:25]=[C:26]([NH2:31])[CH:27]=[CH:28][C:29]=1[Cl:30]>CN(C)C=O>[Cl:23][C:24]1[CH:25]=[C:26]([NH:31][C:7]([C:4]2[CH:3]=[CH:2][N+:1]([O-:10])=[CH:6][CH:5]=2)=[O:9])[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

5

Reactant 3

HCID 72573,4-DichloroanilineHCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 13604807N-(3,4-dichlorophenyl)-4-pyridinecarboxamide-1-oxideYield 70.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 4-pyridinecarboxylic acid-1-oxide (3.74 g, 26.9 mmol) and 1,1'-Carbonyldiimidazole (4.80 g, 29.6 mmol) in dry dimethylformamide (50 ml) was stirred for 40 minutes under an air-lock and treated with 3,4-dichlorobenzenamine (4.79 g, 29.6 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 (80 ml) to give the title compound (5.38 g), m.p. 259°-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 (80 ml)

Sources & evidence

ORD record
ord-ecabbf4affea4746a3a48b865638e7b7
Source dataset
uspto-grants-1988_03
Patent number
US04728658

Linked notes

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