Lithium hydroxide, monohydrate → HCID 14748625, compound

HRID 1089164Notes

Reaction equation

HRID 1089164 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([O:13]CC)=[O:12])[O:7][C:6]=2[CH:5]=[C:4]([C:16]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:21]=[CH:20][CH:19]=2)=[O:17])[C:3]=1[Cl:29].O.[OH-].[Li+]>O1CCCC1.O>[Cl:1][C:2]1[C:10]2[O:9][CH:8]([C:11]([OH:13])=[O:12])[O:7][C:6]=2[CH:5]=[C:4]([C:16]([C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:21]=[CH:20][CH:19]=2)=[O:17])[C:3]=1[Cl:29]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 14748612HCID 14748612, compound

Product 1

HCID 14748625HCID 14748625, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.5 g of ethyl 4,5-dichloro-6-(1-(2-pyridyl)-5-pyrazolylcarbonyl)-1,3-benzodioxole-2-carboxy l ate are dissolved in a mixture of 18 ml of tetrahydrofuran and 2 ml of water. 177 mg of lithium hydroxide monohydrate are added to the solution and the mixture is stirred at room temperature for one hour. The reaction mixture is concentrated under reduced pressure to remove tetrahydrofuran. Water and 1N hydrochloric acid are added to the residue, and the mixture is extracted with ethyl acetate. The extract is washed with water, dried and evaporated under reduced pressure to remove solvent. The residue is recrystallized from ethyl acetate-n-hexane to give 1.35 g of 4,5-dichloro-6-(1-(2-pyridyl)-5-pyrazolylcarbonyl)-1,3-benzodioxol e-2-carboxylic acid. Yield: 96%

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customto remove tetrahydrofuran
  3. additionWater and 1N hydrochloric acid are added to the residue
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe extract is washed with water
  6. customdried
  7. customevaporated under reduced pressure
  8. customto remove solvent
  9. customThe residue is recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-7923e63589e34ba4a55637776f4df678
Source dataset
uspto-grants-1990_10
Patent number
US04965282

Reaction notes

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