Acetic Acid → HCID 67459038, compound

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

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.