Sodium Hydroxide → HCID 178467486, compound

HRID 872920Notes

Reaction equation

HRID 872920 reaction equation
[OH-].[Na+].[CH2:3]([O:5][C:6]1[NH:10][N:9]=[C:8]([C:11]([O-:13])=[O:12])[C:7]=1[CH3:14])[CH3:4]>C(O)C.C1COCC1>[CH2:3]([O:5][C:6]1[NH:10][N:9]=[C:8]([C:11]([OH:13])=[O:12])[C:7]=1[CH3:14])[CH3:4]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178467485HCID 178467485, compound

Product 1

HCID 178467486HCID 178467486, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

2 M solution of sodium hydroxide (98 ml, 197 mmol) was added to a solution of 5-ethoxy-4-methyl-1H-pyrazole-3-carboxylate (7.8 g, 39.4 mmol) in ethanol (70 ml) and THF (30 ml). The reaction mixture was refluxed for 3 h and then the solvents were evaporated and water (200 ml) was added to the residue. It was acidified to pH 1 with conc. HCl and extracted three times with EtOAc. The precipitate formed in the extraction was filtered and washed with EtOAc and the filtrate evaporated to dryness affording 4.2 g (62%) of the title compound. LC-MS: [M+1]=171.17.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customthe solvents were evaporated
  3. additionwater (200 ml) was added to the residue
  4. extractionextracted three times with EtOAc
  5. customThe precipitate formed in the extraction
  6. filtrationwas filtered
  7. washwashed with EtOAc
  8. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-da52bd43008e40ddaeef85001912b6bc
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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