1,2-Dichloroethane → 2-chloro-N-(4-chlorophenyl)pyridine-3-carboxamide

HRID 1787919

Reaction equation

HRID 1787919 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl:25]CCCl>>[Cl:10][C:11]1[CH:17]=[CH:16][C:14]([NH:15][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[N:4][C:3]=2[Cl:25])=[CH:13][CH:12]=1

Participants

5

Reactant 4

HCID 111,2-DichloroethaneHCID 78124-ChloroanilineHCID 8471TriethylamineHCID 82604Nicotinoyl chloride

Product 1

HCID 5879062-chloro-N-(4-chlorophenyl)pyridine-3-carboxamideYield 100%

Procedure

To a solution of nicotinoyl chloride (0.500 g, 2.84 mmol) in 15 mL of 1,2-dichloroethane was added 4-chloroaniline (0.432 g, 3.41 mmol) and triethylamine (0.400 mL, 2.84 mmol), respectively. The reaction mixture was stirred at room temperature for 1 h before it was washed with water (2×), brine (1×), dried over Na2SO4, and the solvent removed in vacuo. The crude material was purified by chromatography over silica, using an eluent of 2% (2 M NH3 in methanol) in chloroform, to afford the amide (0.758 g, 100%).

Workup

  1. washwas washed with water (2×), brine (1×)
  2. dry with materialdried over Na2SO4
  3. customthe solvent removed in vacuo
  4. customThe crude material was purified by chromatography over silica

Sources & evidence

ORD record
ord-ee29ab3c79d147be90897a0680970a2d
Source dataset
uspto-grants-2009_03
Patent number
US07511066B2

Linked notes

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