Lithium Hydroxide → 1-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acid

HRID 2186223

Reaction equation

HRID 2186223 reaction equation
[OH-].[Li+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([O:18]C)=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:7][CH:6]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([S:20][CH3:21])=[N:12]2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 18177273methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate

Product 1

HCID 181773011-(4-Methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylic acidYield 98.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of lithium hydroxide (4.5 mL, 1.0 M, 4.5 mmol) was added to a suspension of methyl 1-(4-methoxyphenyl)-3-methylthio-1H-pyrazole-5-carboxylate (840 mg, 3.0 mmol) in MeOH (30 mL) and stirred at room temperatureerature for 21 hours. The resulting mixture was concentrated and partitioned between EtOAc and H2O. The organic layer was removed, and the aqueous layer was acidified with 1M HCl and extracted twice with EtOAc. The combined organic extracts were dried over Na2SO4, filtered, and evaporated to yield clean product (784 mg, 98%). 1H NMR (CDCl3): δ7.33 (d, 2H, J=8.4), 6.97 (s, 1H), 6.95 (d, 2H, J=8.4), 3.85 (s, 3H), 2.55 (s, 3H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. customThe organic layer was removed
  4. extractionextracted twice with EtOAc
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-dc39abd683fd46579c0c776c93bf457b
Source dataset
uspto-grants-2002_06
Patent number
US06403620B1

Linked notes

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