Sodium Hydroxide → 4-(4-fluorophenyl)-1-methyl-1H-pyrazole-3-carboxylic acid

HRID 1085846Notes

Reaction equation

HRID 1085846 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([O:16]CC)=[O:15])=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:14]([OH:16])=[O:15])=[N:10][N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19768527HCID 19768527, compound

Product 1

HCID 197686484-(4-fluorophenyl)-1-methyl-1H-pyrazole-3-carboxylic acidYield 90.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8.6 g (34.6 mmol) of ethyl 4-(4-fluorophenyl)-1-methyl-3-pyrazolecarboxylate were heated to 70° for 60 minutes with 90 ml of 2N sodium hydroxide solution and 50 ml of water. Conversion into the acid form and recrystallization of the crude product from ethyl acetate/hexane yielded 6.9 g (gO 4%) of 4-(4-fluorophenyl)-1-methyl-3-pyrazolecarboxylic acid as white crystals, melting point 146°-147°.

Workup

  1. customConversion into the acid form and recrystallization of the crude product from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c4eb6286b1a74530bb75d39ec0395447
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

Loading…