Hydrochloric Acid → 3(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-

HRID 1590622Notes

Reaction equation

HRID 1590622 reaction equation
C1(S([C:10]2[N:11]=[N:12][C:13]([C:16]3[C:17]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][N:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=34)=[CH:14][CH:15]=2)(=O)=O)C=CC=CC=1.[OH-:31].[Na+].Cl>O1CCOCC1>[O:31]=[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:18][N:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=23)=[N:12][NH:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 19009010HCID 19009010, compound

Product 1

HCID 105894183(2H)-Pyridazinone, 6-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-Yield 114.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-(3-phenylsulfonylpyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (20.0 g), sodium hydroxide solution (80 ml; containing 7.8 g of sodium hydroxide), and 1,4-dioxane (40 ml) was stirred for 2 hours under reflux. After being cooled to room temperature, the reaction mixture was acidified with 36% hydrochloric acid (15 ml). The precipitate formed was collected, washed with three 25 ml portions of water, and dried to give 3-(3-oxo-2,3-dihydropyridazin-6-yl)-2-phenylpyrazolo[1,5-a]pyridine (16.0 g). An analytical sample was prepared by recrystallization from ethyl acetate.

Workup

  1. temperatureunder reflux
  2. customThe precipitate formed
  3. customwas collected
  4. washwashed with three 25 ml portions of water
  5. customdried

Sources & evidence

ORD record
ord-c15c605c611449f1a9eca9b401d7593f
Source dataset
uspto-grants-1993_04
Patent number
US05204346

Reaction notes

Loading…