Hydrochloric Acid → Methyl 3-(1H-pyrazol-1-yl)benzoate

HRID 399796Notes

Reaction equation

HRID 399796 reaction equation
[NH:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=[O:7])[NH2:2].CO[CH:14](OC)[CH2:15][CH:16](OC)OC.Cl.[CH3:24]O>>[N:1]1([C:3]2[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=2)[C:6]([O:8][CH3:24])=[O:7])[CH:16]=[CH:15][CH:14]=[N:2]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66019TetramethoxypropaneHCID 27365213-Hydrazinobenzoic acid

Product 1

HCID 11171669Methyl 3-(1H-pyrazol-1-yl)benzoate

Procedure

The mixture of 3-hydrazinobenzoic acid (2.0 g), 1,1,3,3-tetramethoxypropane (2.2 ml) and conc. hydrochloric acid (2.4 ml) in methanol (10.0 ml) was heated under reflux for 2 hours, and the mixture was evaporated in vacuo. The residue was dissolved in ethyl acetate, washed with a saturated aqueous sodium bicarbonate solution and brine. The residue was obtained by evaporating solvent, and purified by column chromatography on silica gel eluting with dichloromethane. The fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(pyrazol-1-yl)benzoate (1.33 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customthe mixture was evaporated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with a saturated aqueous sodium bicarbonate solution and brine
  6. customThe residue was obtained
  7. customby evaporating solvent
  8. custompurified by column chromatography on silica gel eluting with dichloromethane
  9. additionThe fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-caee62481758467ba6a97cb4a03d8e99
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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