HCID 69056186, compound → 3-(4-methylphenyl)-1H-indazole

HRID 2108995Notes

Reaction equation

HRID 2108995 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[CH2:15][CH2:14][CH2:13][CH2:12][C:11]=3[NH:10][N:9]=2)=[CH:4][CH:3]=1>C1[C@H]2[C@@H](CCCC2)CCC1.[Pd]>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][N:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69056186HCID 69056186, compound

Product 1

HCID 98777323-(4-methylphenyl)-1H-indazoleYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178420442HCID 178420442, compoundSolvent

Procedure

Into the solution of compound 8 (12.3 g, 0.058 mol) in trans-decahydronaphthalene (trans-decalin) was added 10% Pd/C (2.7 g), and the mixture was heated under reflux for 4 h, and then concentrated in vacuo in oil bath until there were about 20 mL solution left. Petroleum ether (80 mL) was added into the residue while hot, and the mixture was well mixed by shaking. The mixture was allowed to precipitate upon cooling to afford 3-(4-methylphenyl)-1H-indazole (10, 9.85 g, 82% yield).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 h
  3. concentrationconcentrated in vacuo in oil bath until there
  4. waitleft
  5. additionPetroleum ether (80 mL) was added into the residue while hot, and the mixture
  6. additionwas well mixed
  7. customto precipitate
  8. temperatureupon cooling

Sources & evidence

ORD record
ord-93a2cf5479a94d28888e08144c378f28
Source dataset
uspto-grants-2009_04
Patent number
US07514465B2

Reaction notes

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