Sodium Hydroxide → 3-[1-(2-Carboxyethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 466021Notes

Reaction equation

HRID 466021 reaction equation
C[O:2][C:3]([CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][C:10]([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)=[CH:9][C:8]1=[O:28])=[O:4].[OH-].[Na+]>CO>[C:3]([CH2:5][CH2:6][N:7]1[CH2:12][CH2:11][C:10]([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)=[CH:9][C:8]1=[O:28])([OH:4])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 151581253-[1-(2-Methoxycarbonylethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581303-[1-(2-Carboxyethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridineYield 51.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-[1-(2-methoxycarbonylethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (440 mg), 1N sodium hydroxide aqueous solution (3 ml) and methanol (4 ml) was heated under reflux for 1.5 hours. Methanol was evaporated in vacuo and water (20 ml) was added to the residue. The aqueous solution was acidified with 5% hydrochloric acid and precipitates were collected by filtration, washed with water, and then with petroleum ether (5 ml). The precipitates were recrystallized from 95% ethanol to give crystals of 3-[1-(2-carboxyethyl)-2-oxo-1,2,5,6-tetrahydropyridin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (220 mg).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. customMethanol was evaporated in vacuo and water (20 ml)
  4. additionwas added to the residue
  5. customprecipitates
  6. filtrationwere collected by filtration
  7. washwashed with water
  8. customThe precipitates were recrystallized from 95% ethanol

Sources & evidence

ORD record
ord-1eda21b35350439db3abdd8e4547b190
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

Loading…