Ethanol → 3-[3-{(E)-2-carboxyvinyl}pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

HRID 466033Notes

Reaction equation

HRID 466033 reaction equation
OC(C(Cl)(Cl)Cl)[CH2:3][C:4]1[N:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12.[OH-:29].[Na+].[CH2:31]([OH:33])[CH3:32]>>[C:31](/[CH:32]=[CH:3]/[C:4]1[N:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[N:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12)([OH:29])=[O:33]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 151581513-[3-(2-Hydroxy-3,3,3-trichloropropyl)pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

Product 1

HCID 151581523-[3-{(E)-2-carboxyvinyl}pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine

Procedure

To an ethanol (12 ml) solution of 3-[3-(2-hydroxy-3,3,3-trichloropropyl)pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (1.20 g) was added 24% aqueous sodium hydroxide solution (4.8 ml), and refluxed for 5 hours. The reaction mixture was evaporated in vacuo and added 10% hydrochloric acid (12 ml). The precipitates were collected by filtration to give 3-[3-{(E)-2-carboxyvinyl}pyridazin-4-yl]-2-phenylpyrazolo[1,5-a]pyridine (0.64 g).

Workup

  1. temperaturerefluxed for 5 hours
  2. customThe reaction mixture was evaporated in vacuo
  3. additionadded 10% hydrochloric acid (12 ml)
  4. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-6198bf04fde4484098bb6fdd4103f91d
Source dataset
uspto-grants-1992_10
Patent number
US05155114

Reaction notes

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