Lithium hydroxide, monohydrate → HCID 178524946, compound

HRID 20314Notes

Reaction equation

HRID 20314 reaction equation
C([O:3][C:4]([C:6]1[C:10]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])=[CH:9][NH:8][N:7]=1)=[O:5])C.O.[OH-].[Li+]>C1COCC1.O>[Cl:18][C:12]1[CH:13]=[C:14]([Cl:17])[CH:15]=[CH:16][C:11]=1[C:10]1[C:6]([C:4]([OH:5])=[O:3])=[N:7][NH:8][CH:9]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 178470487HCID 178470487, compound

Product 1

HCID 178524946HCID 178524946, compoundYield 108.1%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of 4-(2,4-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (205 mg; 0.72 mmol) and lithium hydroxide monohydrate (125 mg; 2.9 mmol) in 1:1 THF/water (10 ml) was heated at 60° C. overnight. The THF was removed by evaporation, the aqueous phase acidified with 1M hydrochloric acid then extracted with ethyl acetate (20 ml). The ethyl acetate layer was dried (MgSC4), filtered and evaporated to give 200 mg of 4-(2,4-dichloro-phenyl)-1H-pyrazole-3-carboxylic acid. (LC/MS: [M+H]+ 256.85).

Workup

  1. customThe THF was removed by evaporation
  2. extractionthen extracted with ethyl acetate (20 ml)
  3. dry with materialThe ethyl acetate layer was dried (MgSC4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-40216cca89eb4cc9aeba2f712b20c843
Source dataset
uspto-grants-2010_06
Patent number
US07745638B2

Reaction notes

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