Hydrochloric Acid → 1-(4-fluorophenyl)-4-methoxy-1H-pyrazole-3-carboxylic acid

HRID 1465189Notes

Reaction equation

HRID 1465189 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([C:15]([O:17]CC)=[O:16])=[N:9]2)=[CH:4][CH:3]=1.[OH-].[K+].Cl>C(Cl)Cl.CC(O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([C:15]([OH:17])=[O:16])=[N:9]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 66611500Ethyl 1-(4-fluorophenyl)-4-methoxy-pyrazole-3-carboxylate

Product 1

HCID 336766731-(4-fluorophenyl)-4-methoxy-1H-pyrazole-3-carboxylic acidYield 95.3%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

E1 (2 mmol, 1.0 eq.) and KOH (6 mmol, 3.0 eq.) in THF/H2O (1/1, 30 mL) were heated for 2 h at 60° C. The mixture was cooled to RT and then acidified with aq. HCl-solution (1N) to pH=1. The aq. phase was extracted with EtOAc. The combined organic phase was dried over Na2SO4. Removal of the solvent yielded the product E2 as a yellow solid (450 mg, 95%). 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.80 (s, 3H), 7.37 (dd, J=J=9.0 Hz, 2H), 7.87 (dd, J=9.0 Hz, J=4.7 Hz, 2H), 8.40 (s, 1H), 12.72 (br s, 1H). MS (ES) C11H9FN2O3 requires: 236. Found: 237 (M+H)+.

Workup

  1. extractionThe aq. phase was extracted with EtOAc
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-6b16842bd88149a299965647a2ef4ea4
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

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