o-Tolylhydrazinium(1+) chloride → 2-(2-methylphenyl)-4,5,6,7-tetrahydro-2H-indazol-3-amine

HRID 915566Notes

Reaction equation

HRID 915566 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].O=[C:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[C:18]#[N:19]>C(O)C>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:18]([NH2:19])=[C:13]2[C:12]([CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:10]1

Participants

4

Reactant 2

HCID 71554o-Tolylhydrazinium(1+) chlorideHCID 2202972-Oxocyclohexanecarbonitrile

Product 1

HCID 589586072-(2-methylphenyl)-4,5,6,7-tetrahydro-2H-indazol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (2-methylphenyl)hydrazine hydrochloride (464 mg, 2.92 mmol) in ethanol (2 mL) was added 2-oxocyclohexanecarbonitrile (300 mg, 2.44 mmol), and the mixture was heated to 60° C. and stirred for 16 h. The flask was then cooled to rt and the solvent was evaporated to give a solid. The crude residue of 2-(2-methylphenyl)-4,5,6,7-tetrahydro-2H-indazol-3-amine hydrochloride (449 mg, 70%) was used in the next step with no further purification. ES-MS m/z 228.2 (MH+); HPLC RT (min) 1.22.

Workup

  1. temperatureThe flask was then cooled to rt
  2. customthe solvent was evaporated
  3. customto give a solid
  4. customThe crude residue of 2-(2-methylphenyl)-4,5,6,7-tetrahydro-2H-indazol-3-amine hydrochloride (449 mg, 70%) was used in the next step with no further purification

Sources & evidence

ORD record
ord-44bdd4cc2b994cd8b0a7d8bd7cedef24
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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