Sodium Hydroxide → HCID 12274202, compound

HRID 1579445Notes

Reaction equation

HRID 1579445 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH3:21])[C:16]([O:18]CC)=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:2]=12.[OH-].[Na+]>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][C:8]3[CH:14]=[C:13]([CH:15]([CH3:21])[C:16]([OH:18])=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:2]=12

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21568490HCID 21568490, compound

Product 1

HCID 12274202HCID 12274202, compoundYield 88.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3 g of ethyl 2-(5H-[1]benzothiopyrano[2,3-b]pyridin-7-yl)propionate and 0.48 g of sodium hydroxide is dissolved in a mixture of 25 ml of ethanol and 5 ml of water, and the solution is heated under reflux for 1.5 hours. The ethanol is distilled off under reduced pressure, and water is added to the residue. The mixture is made acid with acetic acid, and the crystalline precipitate is filtered off and recrystallized from aqueous dioxane to give 2.4 g of 2-(5H-[1]benzothiopyrano[2,3-b]pyridin-7-yl)propionic acid melting at 203°-204°C.

Workup

  1. temperaturethe solution is heated
  2. temperatureunder reflux for 1.5 hours
  3. distillationThe ethanol is distilled off under reduced pressure, and water
  4. additionis added to the residue
  5. filtrationthe crystalline precipitate is filtered off
  6. customrecrystallized from aqueous dioxane

Sources & evidence

ORD record
ord-d294a1e881a54013a1d28845acee3c39
Source dataset
uspto-grants-1976_01
Patent number
US03931205

Reaction notes

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