Water → 3-(3-Pyridinyl)-5-isoxazolecarboxylic acid

HRID 589622Notes

Reaction equation

HRID 589622 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[O:9][N:8]=2)[CH:2]=1.O.[OH-].[Na+]>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[O:9][N:8]=2)[CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 776521HCID 776521, compound

Product 1

HCID 290785823-(3-Pyridinyl)-5-isoxazolecarboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

300 mg (1.38 mmol) of ethyl 3-(pyridin-3-yl)-1,2-oxazole-5-carboxylate (for preparation see Chem. Heterocyclic Comp. 2000, 36, 1226-1231) were dissolved in 20 ml of dioxane. While cooling with ice, 7 ml of water and 0.35 ml of 45% aqueous sodium hydroxide solution were added to the solution. The mixture was stirred at room temperature for two hours, then the dioxane was removed on a rotary evaporator under reduced pressure. Ice-water was added to the residue, and it was acidified with concentrated hydrochloric acid. The solution was stirred at room temperature overnight, and the precipitated solid was filtered off with suction and dried.

Workup

  1. additionwere added to the solution
  2. customthe dioxane was removed on a rotary evaporator under reduced pressure
  3. additionIce-water was added to the residue, and it
  4. stirringThe solution was stirred at room temperature overnight
  5. filtrationthe precipitated solid was filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-f795165e54a5481097bbdd1e2d72c3c2
Source dataset
uspto-grants-2016_01
Patent number
US09233951B2

Reaction notes

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