Sodium Hydroxide → HCID 178525590, compound

HRID 703983Notes

Reaction equation

HRID 703983 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][N:7]1[C:11]([OH:12])=[CH:10][C:9]([C:13]2[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=23)=[N:8]1)=[O:4].[OH-].[Na+]>C(O)C>[C:3]([CH2:5][CH2:6][N:7]1[C:11]([OH:12])=[CH:10][C:9]([C:13]2[C:14]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:15][N:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=23)=[N:8]1)([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178500743HCID 178500743, compound

Product 1

HCID 178525590HCID 178525590, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3-[1-(2-methoxycarbonylethyl)-5-hydroxypyrazol-3-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.50 g), 1N sodium hydroxide aqueous solution (3 ml) and ethanol (5 ml) was heated under reflux for 2.5 hours. Ethanol was evaporated in vacuo. The residue was acidified with 5% hydrochloric acid and extracted with chloroform (25 ml×2). Combined extract was washed with a saturated aqueous solution of sodium chloride (25 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel using a mixture of chloroform and methanol (30:1) as an eluent and recrystallized from ethanol to give crystal of 3-[1-(2-carboxyethyl)-5-hydroxypyrazol-3-yl]-2-phenylpyrazolo[1,5-a]pyridine (141 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. customEthanol was evaporated in vacuo
  4. extractionextracted with chloroform (25 ml×2)
  5. extractionCombined extract
  6. washwas washed with a saturated aqueous solution of sodium chloride (25 ml)
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel using
  10. additiona mixture of chloroform and methanol (30:1) as an eluent
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a4edf8137f4c41328e7d5731ee911d27
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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