Acetic Acid → HCID 67459038, compound

HRID 2366493Notes

Reaction equation

HRID 2366493 reaction equation
C(O)(=O)C.O.[NH2:6]N.C[N:9]([CH:11]=[C:12]1[C:17](=O)[C:16]([CH3:20])([CH3:19])[CH2:15][CH2:14][C:13]1=[O:21])C>C(O)CCC>[CH3:19][C:16]1([CH3:20])[C:17]2[NH:6][N:9]=[CH:11][C:12]=2[C:13](=[O:21])[CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 67458045HCID 67458045, compound

Product 1

HCID 67459038HCID 67459038, compoundYield 51.1%

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 (150 mmol, 7.25 mL), were added slowly to a solution of 2-((dimethylamino)methylene)-4,4-dimethylcyclohexane-1,3-dione (150 mmol, 29.2 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 7,7-dimethyl-6,7-dihydro-1H-indazol-4(5H)-one (76.7 mmol, 12.6 g, 51%) 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-a3eb215107db4751891811442d176059
Source dataset
uspto-grants-2014_04
Patent number
US08697744B2

Reaction notes

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