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

HRID 245813Notes

Reaction equation

HRID 245813 reaction equation
O/[CH:2]=[C:3]1\[C:4](=O)[CH2:5][CH2:6][C:7]([CH3:10])([CH3:9])[CH2:8]\1.[NH2:12][NH2:13]>CO>[CH3:9][C:7]1([CH3:10])[CH2:6][CH2:5][C:4]2[NH:13][N:12]=[CH:2][C:3]=2[CH2:8]1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 583881822-[1-hydroxy-meth-(Z)-ylidene]-4,4-dimethyl-cyclohexanone

Product 1

HCID 894210185,5-dimethyl-4,5,6,7-tetrahydro-1H-indazoleYield 83%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 100 ml round-bottomed flask, 2-[1-hydroxy-meth-(Z)-ylidene]-4,4-dimethyl-cyclohexanone (1.30 g, 8.43 mmol) was dissolved in methanol (8.5 ml). Hydrazine (0.27 ml, 8.43 mmol) was added very slowly which resulted in an exothermic reaction. The reaction mixture was stirred at room temperature for 50 min then concentrated. The residue was triturated with petroleum ether to afford 1.05 g (83%) of 5,5-dimethyl-4,5,6,7-tetrahydro-1H-indazole as a light brown solid. 1H NMR (CDCl3, 300 MHz): δ (ppm) 7.28 (s, 1H), 2.67 (t, J=6.6 Hz, 2H), 2.32 (s, 2H), 1.60 (t, J=6.6 Hz, 2H), 0.99 (s, 6H).

Workup

  1. customresulted in an exothermic reaction
  2. concentrationthen concentrated
  3. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-bae5aa8a471048f6ad57d500cbe3fd6c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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