Pyridine → HCID 23125016, compound

HRID 2223368Notes

Reaction equation

HRID 2223368 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=1.N1C=CC=CC=1>C(Cl)(Cl)Cl.CN(C)C=O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([NH:30][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([C:13]([F:16])([F:15])[F:14])=[CH:12][C:4]=2[N+:1]([O-:3])=[O:2])=[N:28][CH:29]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 65578Oxalyl chlorideHCID 661742-Amino-5-chloropyridineHCID 6420962-Nitro-4-(trifluoromethyl)benzoic acid

Product 1

HCID 23125016HCID 23125016, compoundYield 112.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6212ChloroformSolvent2×

Procedure

2-Nitro-4-(trifluoromethyl)benzoic acid (3.0 g) is suspended in chloroform (25 ml), and thereto are added oxalyl chloride (1.67 ml) and N,N-dimethylformamide (2 drops) followed by stirring at room temperature for 3 hours. The reaction solution is concentrated under reduced pressure, and to the residue is poured chloroform (20 ml) to obtain a suspension. Chloroform (30 ml) is added to 5-chloro-2-aminopyridine (1.56 g) and pyridine (1.55 ml), and the solution is ice-cooled. To the solution is added dropwise the suspension prepared above. The reaction solution is stirred at room temperature for 8 hours and concentrated under reduced pressure. The residue is diluted with ethyl acetate, washed successively with 10% aqueous potassium hydrogen sulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over magnesium sulfate, and evaporated to remove the solvent under reduced pressure. The resulting residue is suspended into n-hexane, filtered and dried to give N-(5-chloropyridin-2-yl)-2-nitro-4-(trifluoromethyl)-benzamide (4.73 g). APCI-MS M/Z: 346/348[M+H]+

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. additionto the residue is poured chloroform (20 ml)
  3. customto obtain a suspension
  4. temperaturecooled
  5. additionTo the solution is added dropwise the suspension
  6. customprepared above
  7. stirringThe reaction solution is stirred at room temperature for 8 hours
  8. concentrationconcentrated under reduced pressure
  9. additionThe residue is diluted with ethyl acetate
  10. washwashed successively with 10% aqueous potassium hydrogen sulfate solution, saturated aqueous sodium hydrogen carbonate solution and saturated brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated
  13. customto remove the solvent under reduced pressure
  14. filtrationfiltered
  15. customdried

Sources & evidence

ORD record
ord-2adb657a03ca4133801a31988d47e8d3
Source dataset
uspto-grants-2008_05
Patent number
US07375119B2

Reaction notes

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