Hydrochloric Acid → 3-(3-Carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

HRID 703980Notes

Reaction equation

HRID 703980 reaction equation
C(C1[C:4](=[O:24])[NH:5][CH:6]=[C:7]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:8]=1)#N.[OH-:25].[K+].Cl.[CH2:28]([OH:30])[CH3:29]>>[C:28]([C:29]1[C:4](=[O:24])[NH:5][CH:6]=[C:7]([C:9]2[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)[CH:8]=1)([OH:25])=[O:30]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 151581163-(3-Cyano-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581293-(3-Carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine

Procedure

A mixture of 3-(3-cyano-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.60 g) and 85% potassium hydroxide (0.38 g) in 67% aqueous ethanol (6 ml) was refluxed for 4 hours. After cooling, the reaction mixture was added onto ice (12 g) and acidified with 5% hydrochloric acid. Precipitates were collected and recrystallized from a mixture of N,N-dimethylformamide and water twice to give 3-(3-carboxy-2-oxo-1,2-dihydropyridin-5-yl)-2-phenylpyrazolo[1,5-a]pyridine (0.36 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. additionthe reaction mixture was added onto ice (12 g)
  4. customPrecipitates
  5. customwere collected
  6. customrecrystallized from a mixture of N,N-dimethylformamide and water twice

Sources & evidence

ORD record
ord-1c08da57c2114b4c93d2db4d3588ee50
Source dataset
uspto-grants-1991_01
Patent number
US04985444

Reaction notes

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