Acetic Acid → HCID 19712410, compound

HRID 2366489Notes

Reaction equation

HRID 2366489 reaction equation
C(O)(=O)C.O.[NH2:6]N.C[N:9]([CH:11]=[C:12]1[C:17](=O)[CH2:16][C:15]([CH3:20])([CH3:19])[CH2:14][C:13]1=[O:21])C>C(O)CCC>[CH3:19][C:15]1([CH3:20])[CH2:16][C:17]2[NH:6][N:9]=[CH:11][C:12]=2[C:13](=[O:21])[CH2:14]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 6898502-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione

Product 1

HCID 19712410HCID 19712410, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

According to Scheme 2 Step 2: At 0° C., acetic acid (8.55 mL) followed by hydrazine monohydrate (197 mmol, 11.3 mL), were added slowly to a solution of 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione (197 mmol, 38.5 g) in butanol (400 mL). The reaction mixture was stirred under reflux for 16 hours. After evaporation of the filtrate, the crude residue was purified by flash chromatography over silica gel cyclohexane/AcOEt (100:0 to 50:50) and then over C18 gel using water/MeOH (100:0 to 50:50) as eluent to yield 6,6-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one (76.7 mmol, 12.6 g, 39%) as a pale yellow solid.

Workup

  1. customAt 0° C.
  2. temperatureunder reflux for 16 hours
  3. customAfter evaporation of the filtrate
  4. customthe crude residue was purified by flash chromatography over silica gel cyclohexane/AcOEt (100:0 to 50:50)

Sources & evidence

ORD record
ord-a2581a20df574c75914ba7e1460ee964
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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