Sodium Hydroxide → HCID 20321543, compound

HRID 866507Notes

Reaction equation

HRID 866507 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:18])[N:10]=[CH:11][C:12]=2[C:13]([O:15]CC)=[O:14])=[C:4]([CH:19]([O:27][CH3:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1.[OH-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:18])[N:10]=[CH:11][C:12]=2[C:13]([OH:15])=[O:14])=[C:4]([CH:19]([O:27][CH3:28])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20321551HCID 20321551, compound

Product 1

HCID 20321543HCID 20321543, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The starting material is prepared analogously as the 2-fluoro analog of Example 6.77 g of 3-[4-chloro-2-(2-chloro-α-methoxy-benzyl)-phenyl]-ethoxycarbonyl-2-methyl-pyrazole are dissolved in 900 ml of ethanol and 240 ml of N aqueous sodium hydroxide and the solution is refluxed for 2 hours. After cooling the aqueous phase is separated, washed with diethyl ether and acidified with hydrochloric acid. It is extracted with methylene chloride, the extract dried and evaporated. The residue is recrystallized from 200 ml of diethyl ether to yield the 3-[4-chloro-2-(2-chloro-α-methoxy-benzyl)-phenyl]-2-methylpyrazole-4-carboxylic acid melting at 210°-213°.

Workup

  1. temperatureAfter cooling the aqueous phase
  2. customis separated
  3. washwashed with diethyl ether
  4. extractionIt is extracted with methylene chloride
  5. customthe extract dried
  6. customevaporated
  7. customThe residue is recrystallized from 200 ml of diethyl ether

Sources & evidence

ORD record
ord-7dace9fa0306483196075fb9e51ef654
Source dataset
uspto-grants-1978_07
Patent number
US04099012

Reaction notes

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