3-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester → 3-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid

HRID 1468177Notes

Reaction equation

HRID 1468177 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[CH:18][CH:17]=3)[CH:13]=[N:12]2)[CH:5]=1>CO.O>[C:22]([C:19]1[CH:18]=[CH:17][C:16]([C:14]2[CH:13]=[N:12][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])[CH:15]=2)=[CH:21][CH:20]=1)#[N:23]

Participants

3

Reactant 1

HCID 675085333-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester

Product 1

HCID 675082023-[4-(4-Cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acidYield 82.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Add LiOH monohydrate (0.03 g, 0.8 mmol) to a suspension of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid methyl ester (0.2 g, 0.6 mmol) in 5 mL of a 4:1 MeOH-water mixture and stir the reaction at room temperature overnight. Concentrate the reaction to remove most of the MeOH, dilute with additional H2O and neutralize by the addition of 1 N aqueous HCl. Isolate the resulting solid by filtration and dry to afford 0.15 g, 71% yield of 3-[4-(4-cyano-phenyl)-pyrazol-1-ylmethyl]-benzoic acid.

Workup

  1. customthe reaction at room temperature overnight
  2. concentrationConcentrate
  3. customthe reaction
  4. customto remove most of the MeOH
  5. additiondilute with additional H2O and neutralize by the addition of 1 N aqueous HCl
  6. customIsolate the resulting solid
  7. filtrationby filtration
  8. customdry

Sources & evidence

ORD record
ord-e61d724ed5f14b7782df7400fb053c02
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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