Sodium Hydroxide → 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid

HRID 1616566Notes

Reaction equation

HRID 1616566 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[O:24][CH3:25])=[N:14]1)C>CO>[CH3:25][O:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[CH:16]=[CH:17][N:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]([OH:26])=[O:5])[N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 684889907-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester

Product 1

HCID 684900687-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acidYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add 2 N sodium hydroxide (20 mL) to a solution of 7-[3-(2-Methoxyphenyl)pyrazol-1-yl]heptanoic acid ethyl ester (3.75 g, 11.4 mmol) in methanol (40 mL) at room temperature under nitrogen and stir the mixture for 8 hours. Remove the solvent under reduced pressure, dilute the residue with water (100 mL), acidify to pH 3 with 1 N HCl, extract with ethyl acetate (200 mL), and dry over sodium sulfate. Remove the solvent under reduced pressure to provide 7-[3-(2-methoxyphenyl)pyrazol-1-yl]heptanoic acid (3.06 g, 89%). APCI mass spectrum m/z 303 [C17H22N2O3+H]+.

Workup

  1. customRemove the solvent under reduced pressure
  2. additiondilute the residue with water (100 mL)
  3. extractionextract with ethyl acetate (200 mL)
  4. dry with materialdry over sodium sulfate
  5. customRemove the solvent under reduced pressure

Sources & evidence

ORD record
ord-3924f31616874ab697473abbbd0534a1
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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