Formic Acid → 2-chloro-5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridine

HRID 1020960Notes

Reaction equation

HRID 1020960 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6](=[NH:10])[NH:7][NH:8][CH3:9])=[CH:4][N:3]=1.[CH:13](O)=O>>[Cl:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]2[N:10]=[CH:9][N:8]([CH3:13])[N:7]=2)=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 178486234HCID 178486234, compound

Product 1

HCID 583719812-chloro-5-(1-methyl-1H-1,2,4-triazol-3-yl)pyridine

Procedure

A solution of 6-chloro-N′-methylnicotinimidohydrazide (2BX) (2.4 g, 13 mmol) in Formic Acid (99%, 10 ml) was stirred at reflux temperature for 1 hour. Reaction was cooled and solvent evaporated. The residue was extracted with EtOAc (100 ml) and Aqueous NaHCO3 (50 ml), organic layer was separated, dried over Na2SO4, filtered and solvent evaporated. The residue chromatographed on silica gel eluting with 10% MeOH:CH2Cl2 yielding title product as a solid (1.8 g, 72%) MS (MH, 195)

Workup

  1. temperatureat reflux temperature for 1 hour
  2. customReaction
  3. temperaturewas cooled
  4. customsolvent evaporated
  5. extractionThe residue was extracted with EtOAc (100 ml) and Aqueous NaHCO3 (50 ml), organic layer
  6. customwas separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customsolvent evaporated
  10. customThe residue chromatographed on silica gel eluting with 10% MeOH

Sources & evidence

ORD record
ord-c1e9ac40f24a4d8f80f3dd529db49809
Source dataset
uspto-grants-2014_05
Patent number
US08716483B2

Reaction notes

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