Hydrochloric Acid → HCID 17947723, compound

HRID 604296Notes

Reaction equation

HRID 604296 reaction equation
Cl.Cl.[F:3][C:4]1[CH:5]=[C:6]([NH:10][NH2:11])[CH:7]=[CH:8][CH:9]=1>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([N:10]2[CH:5]=[CH:4][C:9]([CH3:8])=[N:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 27239143-Fluorophenylhydrazine hydrochloride

Product 1

HCID 17947723HCID 17947723, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add hydrochloric acid (5M, 12 mL, 60 mmol) to a mixture of 4,4-dimethoxybuta-2-one (6.61 g, 6.67 mL, 50 mmol) and 3-fluorophenylhydrazine hydrochloride (8.13 g, 50 mmol) in ethanol (50 mL). Heat and stir under reflux under nitrogen for 7.5 hr., cool to room temperature, allow to stand for 60 hr. Evaporate the ethanol in vacuo, and chromatograph the residue on silica eluting with DCM. Evaporate the dichlormethane to give 1-(3-fluoro-phenyl)-3-methyl-1H-pyrazole as a liquid (4.38 g, 49%). MS (m/z): 171.1 (M+1).

Workup

  1. temperatureHeat
  2. temperatureunder reflux under nitrogen for 7.5 hr
  3. customEvaporate the ethanol in vacuo, and chromatograph the residue on silica eluting with DCM
  4. customEvaporate the dichlormethane

Sources & evidence

ORD record
ord-65f4f11484064b4bb3e005cf811a2afb
Source dataset
uspto-grants-2011_03
Patent number
US07910588B2

Reaction notes

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