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

HRID 703981Notes

Reaction equation

HRID 703981 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-f505f025724646898ae991b0fda9ef4f
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

Loading…