Hydrochloric Acid → 4-cyano-3-(1H-pyrazol-1-yl)benzoic acid

HRID 587851Notes

Reaction equation

HRID 587851 reaction equation
[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[N:13]1[CH:17]=[CH:16][CH:15]=[N:14]1)#[N:2].Cl>O1CCCC1.O.[OH-].[Li+].O>[C:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N:13]1[CH:17]=[CH:16][CH:15]=[N:14]1)#[N:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 66973486methyl 4-cyano-3-(1H-pyrazol-1-yl)benzoate

Product 1

HCID 669737514-cyano-3-(1H-pyrazol-1-yl)benzoic acidYield 90.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 168937Lithium hydroxide, monohydrateSolvent

Procedure

Methyl 4-cyano-3-(1H-pyrazol-1-yl)benzoate (0.27 g) was dissolved in tetrahydrofuran (10 ml). To the solution, a solution in which lithium hydroxide monohydrate (0.10 g) is dissolved in water (10 ml) was added at room temperature. The reaction mixture was stirred for 2 hours. The reaction solution was acidified with 2 N hydrochloric acid, and then extracted twice with ethyl acetate. The organic phases were combined, washed with water, and then dried over anhydrous sodium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a crude product of 4-cyano-3-(1H-pyrazol-1-yl)benzoic acid (0.23 g). The crude product was used for the next step without further purification.

Workup

  1. additionwas added at room temperature
  2. extractionextracted twice with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe drying agent was removed by filtration
  6. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9c6801c31bc441b5939dc4819555341a
Source dataset
uspto-grants-2016_01
Patent number
US09227923B2

Reaction notes

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