Sodium Hydroxide → HCID 178463029, compound

HRID 2268047Notes

Reaction equation

HRID 2268047 reaction equation
C([O:3][C:4]([C:6]1[C:7]([OH:17])=[C:8]2[CH:14]=[N:13][N:12]([CH2:15][CH3:16])[C:9]2=[N:10][CH:11]=1)=[O:5])C.[OH-].[Na+]>CCO.O>[CH2:15]([N:12]1[C:9]2=[N:10][CH:11]=[C:6]([C:4]([OH:5])=[O:3])[C:7]([OH:17])=[C:8]2[CH:14]=[N:13]1)[CH3:16]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178469631HCID 178469631, compound

Product 1

HCID 178463029HCID 178463029, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Ethyl-4-hydroxy-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl ester (10.0 g, 42.6 mmol) was suspended in 50 mL EtOH. To this suspension was added 6 N NaOH (21.3 mL, 3 eq). The resulting light brown solution was heated at reflux for 3 hr before being diluted with 100 mL water. The aqueous solution was extracted with diethyl ether (50 mL×3) and the organic layer was discarded. The aqueous layer was acidified with 1 N HCl and a white precipitate formed. The title compound was collected by filtration and rinsed with water and diethyl ether affording a white solid (7.9 g, 90%): mp 218° C. (decomposed); LRMS (m/z) 208 (MH+).

Workup

  1. temperatureThe resulting light brown solution was heated
  2. temperatureat reflux for 3 hr
  3. extractionThe aqueous solution was extracted with diethyl ether (50 mL×3)
  4. customa white precipitate formed
  5. filtrationThe title compound was collected by filtration
  6. washrinsed with water and diethyl ether affording a white solid (7.9 g, 90%)

Sources & evidence

ORD record
ord-818b136eb44649f4971da086d0b4e95b
Source dataset
uspto-grants-2001_12
Patent number
US06326379B1

Reaction notes

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