Hydrochloric Acid → 3-Benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylic acid

HRID 2102260Notes

Reaction equation

HRID 2102260 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([C:14]([O:16]CC)=[O:15])=[C:12]([Br:19])[N:11]([CH:20]([CH3:22])[CH3:21])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCOCC1>[CH2:1]([O:8][C:9]1[C:13]([C:14]([OH:16])=[O:15])=[C:12]([Br:19])[N:11]([CH:20]([CH3:22])[CH3:21])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 23113375HCID 23113375, compound

Product 1

HCID 230795363-Benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylic acidYield 64.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 3-benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylate (7.7 g) was suspended in 1,4-dioxane (19 mL) and 20% sodium hydroxide aqueous solution (19 mL) was added to the suspension. The mixture was stirred at 100° C. for 8 hours. After the reaction mixture was cooled, the reaction mixture was poured into 2 mol/L hydrochloric acid (100 mL) and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 4.6 g of the title compound.

Workup

  1. temperatureAfter the reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-cb4abe983e9e4c80abe4022d4321b293
Source dataset
uspto-grants-2009_08
Patent number
US07576064B2

Reaction notes

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