Lithium hydroxide, monohydrate → HCID 178524946, compound

HRID 2170582Notes

Reaction equation

HRID 2170582 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 (MgSO4), 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 (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-3829806477864c69af8b3bf7396a6898
Source dataset
uspto-grants-2015_06
Patent number
US09051278B2

Reaction notes

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