Hydrochloric Acid → HCID 14796396, compound

HRID 1084845Notes

Reaction equation

HRID 1084845 reaction equation
[OH-].[Na+].C(O)C.[C:6]1([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[C:14]([C:21]3[CH:33]=[CH:32][C:24]([O:25][CH2:26][C:27]([O:29]CC)=[O:28])=[CH:23][CH:22]=3)=[N:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>O.O1CCOCC1>[C:6]1([N:12]2[C:16]3=[N:17][CH:18]=[CH:19][CH:20]=[C:15]3[C:14]([C:21]3[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:32][CH:33]=3)=[N:13]2)[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 14796395HCID 14796395, compound

Product 1

HCID 14796396HCID 14796396, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

In 300 ml of water was dissolved 5.1 g of sodium hydroxide, and 800 ml of ethanol was added to the solution. While stirring, thereto was added a solution of 40 g of ethyl 4-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-3-yl)phenoxyacetate dissolved in 200 ml of dioxane. After the mixture was stirred at room temperature for 4 hours, it was poured into about 3 l of cold water. The mixture was neutralized by the addition of dilute hydrochloric acid. The resulting crystals were collected by filtration and recrystallized from hydrous dioxane to give 22.1 g of 4-(1-phenyl-1H-pyrazolo[3,4-b]pyridin-3-yl)phenoxyacetic acid, m.p. 220°-222° C.

Workup

  1. additionwas added to the solution
  2. stirringAfter the mixture was stirred at room temperature for 4 hours
  3. filtrationThe resulting crystals were collected by filtration
  4. customrecrystallized from hydrous dioxane

Sources & evidence

ORD record
ord-e4e024f0d10d49d798af2c791cfe9a07
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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