Hydrochloric Acid → 1-(3-Chloro-4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acid

HRID 2067949Notes

Reaction equation

HRID 2067949 reaction equation
C([O:5][C:6]([C:8]1[CH:9]=[N:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[C:16]([Cl:21])[CH:15]=2)[C:12]=1[CH3:13])=[O:7])(C)(C)C.Cl.O1CCOCC1>>[Cl:21][C:16]1[CH:15]=[C:14]([N:11]2[C:12]([CH3:13])=[C:8]([C:6]([OH:7])=[O:5])[CH:9]=[N:10]2)[CH:19]=[CH:18][C:17]=1[F:20]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 584433921-(3-chloro-4-fluoro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid tert-butyl ester

Product 1

HCID 222279051-(3-Chloro-4-fluorophenyl)-5-methyl-1H-pyrazole-4-carboxylic acidYield 31.2%

Procedure

1-(3-Chloro-4-fluoro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid tert-butyl ester (2.1 g, 6.8 mmol) is treated with cold HCl in dioxane (4.0 N solution, 10 mL, 40 mmol) and stirred for 16 hours at room temperature. The resultant precipitate is collected by filtration, washed with dioxane (2×1 mL) and dried to afford 1-(3-chloro-4-fluoro-phenyl)-5-methyl-1H-pyrazole-4-carboxylic acid as a tan solid (540 mg, 31%).

Workup

  1. filtrationThe resultant precipitate is collected by filtration
  2. washwashed with dioxane (2×1 mL)
  3. customdried

Sources & evidence

ORD record
ord-9c5d521c3304472b9695ab51980b7ccb
Source dataset
uspto-grants-2012_10
Patent number
US08293917B2

Reaction notes

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