Methanol → HCID 21250760, compound

HRID 1655265Notes

Reaction equation

HRID 1655265 reaction equation
Br[CH2:2][C:3]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]([CH3:12])[N:4]=1.[CH3:13][OH:14]>[N+]([O-])([O-])=O.[Ag+]>[Cl:11][C:6]1[N:5]([CH3:12])[N:4]=[C:3]([CH2:2][O:14][CH3:13])[C:7]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 102643161H-Pyrazole, 3-(bromomethyl)-5-chloro-1-methyl-4-nitro-

Product 1

HCID 21250760HCID 21250760, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 24470Silver NitrateCatalyst

Procedure

A solution of 3-bromomethyl-5-chloro-1-methyl-4-nitropyrazole (5.0 g, 19.6 mmol) in methanol (50 ml) was treated with silver nitrate (5.75 g, 33.8 mmol) and the mixture heated under reflux for 2 hours. The cooled reaction mixture was filtered and the filtrate evaporated under vacuum. The residue was partitioned between ethyl acetate (100 ml) and water (50 ml) and the aqueous phase extracted with a further quantity of ethyl acetate (50 ml). The organic extracts were combined, dried (MgSO4) and evaporated under vacuum. Chromatography on silica gel, eluting with a 97:3 mixture of dichloromethane and methanol, gave the title pyrazole as a white solid (1.6 g, 40%), m.p. 59°-63° C. Found: C,34.65; H,3.83; N,20.05. C6H8ClN3O3 requires C,35.05; H,3.92; N,20.44%.

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 2 hours
  3. customThe cooled reaction mixture
  4. filtrationwas filtered
  5. customthe filtrate evaporated under vacuum
  6. customThe residue was partitioned between ethyl acetate (100 ml) and water (50 ml)
  7. extractionthe aqueous phase extracted with a further quantity of ethyl acetate (50 ml)
  8. dry with materialdried (MgSO4)
  9. customevaporated under vacuum
  10. washChromatography on silica gel, eluting with a 97:3 mixture of dichloromethane and methanol

Sources & evidence

ORD record
ord-d90e65fca8314266b317b9e22c407fc0
Source dataset
uspto-grants-1993_10
Patent number
US05250534

Reaction notes

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