Hydrazine → 6,6-Dimethyl-4,5,6,7-tetrahydro-1H-indazole

HRID 245973Notes

Reaction equation

HRID 245973 reaction equation
O/[CH:2]=[C:3]1\[C:4](=O)[CH2:5][C:6]([CH3:10])([CH3:9])[CH2:7][CH2:8]\1.[NH2:12][NH2:13]>CO>[CH3:9][C:6]1([CH3:10])[CH2:5][C:4]2[NH:13][N:12]=[CH:2][C:3]=2[CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 89421039HCID 89421039, compound

Product 1

HCID 585504376,6-Dimethyl-4,5,6,7-tetrahydro-1H-indazoleYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-[1-hydroxy-meth-(Z)-ylidene]-5,5-dimethyl-cyclohexanone (1.64 g, 10.6 mmol) in MeOH (10 mL) was added hydrazine (0.33 mL, 10.6 mmol) dropwise. The exothermic reaction was controlled by intermitant use of an ice bath. The yellow reaction mixture was stirred at room temperature for 30 min then concentrated. The residue was dissolved in CH2Cl2 and washed with water. The organic layer was dried over MgSO4 and concentrated to afford 1.53 g (96%) of 6,6-dimethyl-4,5,6,7-tetrahydro-1H-indazole as a yellow solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.32 (s, 1H), 2.55 (t, J=6.4 Hz, 2H), 2.44 (s, 2H), 1.53 (t, J=6.4 Hz, 2H), 1.01 (s, 6H).

Workup

  1. customThe exothermic reaction
  2. customwas controlled by intermitant use of an ice bath
  3. concentrationthen concentrated
  4. dissolutionThe residue was dissolved in CH2Cl2
  5. washwashed with water
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5ac2f217b8a04778a71cffec92c50d1a
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

Loading…