Hydrochloric Acid → HCID 69205543, compound

HRID 30632Notes

Reaction equation

HRID 30632 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]\[C:16]([O:18]C)=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH3:13])[N:11]=[CH:10][C:9]=2/[CH:14]=[CH:15]\[C:16]([OH:18])=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86602516methyl (2Z)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylate

Product 1

HCID 69205543HCID 69205543, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of methyl (2Z)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylate (300 mg), methanol (5 mL) and a 1N aqueous sodium hydroxide solution (5 mL) was stirred at 60° C. for 30 min. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated. Recrystallization of the residue from ethyl acetate-hexane gave (2Z)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid as crystals (220 mg, yield 78%). melting point: 205-206° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customRecrystallization of the residue from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9aaf18b67096441dbce0ca5b8bc5c07a
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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