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

HRID 1039180Notes

Reaction equation

HRID 1039180 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-a008d378880c4185aefe940e1497e598
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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