Hydrochloric Acid → methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate

HRID 1295274Notes

Reaction equation

HRID 1295274 reaction equation
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].C.[C:25](=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:25])=[O:15])[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 20975526HCID 20975526, compoundHCID 22930700HCID 22930700, compound

Product 1

HCID 22930789methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylic acid (33.00 g), methane iodide (8.5 ml), potassium carbonate (18.88 g) and N,N-dimethylformamide (300 ml) was stirred overnight at room temperature. The reaction mixture was poured into dilute hydrochloric acid and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (33.48 g, yield 97%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 53–54° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-641406eb15df4e1496a80c04ecb1c8ac
Source dataset
uspto-grants-2007_07
Patent number
US07241785B2

Reaction notes

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