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

HRID 53519
Notes
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Reaction equation

HRID 53519 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 31275
1,4-Dioxane
Solvent

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-347bb4d39b864da4bcaa306b0d10cdd3
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05620974

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes