Pyridine → 2-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamide

HRID 2380233Notes

Reaction equation

HRID 2380233 reaction equation
[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=1[CH3:8].[Cl:10][C:11]1[N:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](Cl)=[O:14].N1C=CC=CC=1.C1CCCCC1>O1CCOCC1>[Cl:10][C:11]1[C:12]([C:13]([NH:1][C:2]2[C:3]([Cl:9])=[N:4][CH:5]=[CH:6][C:7]=2[CH3:8])=[O:14])=[CH:16][CH:17]=[CH:18][N:19]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8078CyclohexaneHCID 27563873-Amino-2-chloro-4-methylpyridineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 104238682-Chloro-N-(2-chloro-4-methyl-3-pyridinyl)-3-pyridinecarboxamideYield 4.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using a procedure analogous to that described in Example 1a, the carboxamide was prepared from 12.8 g of 3-amino-2-chloro-4-methyl pyridine, 15.8 g of 2-chloronicotinoyl chloride, 7.1 g of pyridine, 30 ml of cyclohexane and 60 ml of dioxane. After removal of the solvent, the product was dissolved in methylene chloride, washed with water and dried (sodium sulfate). After removal of the solvent, the residue was washed with ethyl acetate to give 1.2 g of the title compound, m.p. 193°-194° C.

Workup

  1. customAfter removal of the solvent
  2. dissolutionthe product was dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried (sodium sulfate)
  5. customAfter removal of the solvent
  6. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-583b49c380194ee4b4288195ccfa1a23
Source dataset
uspto-grants-1994_11
Patent number
US05366972

Reaction notes

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