Acetic Acid → 1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one

HRID 62447

Reaction equation

HRID 62447 reaction equation
C[N:2]([CH:4]=[C:5]1[C:10](=O)[CH2:9][CH2:8][CH2:7][C:6]1=[O:12])C.[S:13]([NH:23]N)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14].CC(O)=O>CCO>[S:13]([N:23]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=[O:12])[C:5]=2[CH:4]=[N:2]1)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 15303P-ToluenesulfonylhydrazideHCID 3593532-[(Dimethylamino)methylidene]cyclohexane-1,3-dione

Product 1

HCID 674585881-tosyl-6,7-dihydro-1H-indazol-4(5H)-oneYield 51.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-((dimethylamino)methylene)cyclohexane-1,3-dione (55 g, 0.329 mol), 2-tosylhydrazine (61.3 g, 0.329 mol) and AcOH (33 mL) in EtOH (540 mL) was heated for 4 h at 70° C. Removed the solvent under reduced pressure and the residue was recrystallized using PE/EA=5/1 to give 1-tosyl-6,7-dihydro-1H-indazol-4(5H)-one (49 g, yield 51.3%) as a white solid.

Workup

  1. customRemoved the solvent under reduced pressure
  2. customthe residue was recrystallized

Sources & evidence

ORD record
ord-ecfba064d9a14925a662eb32c5e86b69
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Linked notes

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