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

HRID 2102332Notes

Reaction equation

HRID 2102332 reaction equation
C([O:3][C:4]([C:6]1[C:7]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:8][N:9]([CH:12]([CH3:14])[CH3:13])[C:10]=1[Br:11])=[O:5])C.[OH-].[Na+].Cl>O1CCOCC1>[CH2:16]([O:15][C:7]1[C:6]([C:4]([OH:5])=[O:3])=[C:10]([Br:11])[N:9]([CH:12]([CH3:14])[CH3:13])[N:8]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=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

3-Benzyloxy-5-bromo-1-isopropylpyrazole-4-carboxylic acid ethyl ester (7.7 g) was suspended into 1,4-dioxan (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 mixture was cooled, the reaction mixture was poured into 2 mol/L hydrochloric acid (100 mL). 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 the title compound (4.6 g).

Workup

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

Sources & evidence

ORD record
ord-e97216e061d84bcd8f5f3375cee8cc79
Source dataset
uspto-grants-2009_08
Patent number
US07576063B2

Reaction notes

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