Cyclohexanone, 2-(hydroxymethylene)- → HCID 71253453, compound

HRID 1029003

Reaction equation

HRID 1029003 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][NH2:10].O[CH:12]=[C:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C:14]1=O>C(O)C>[Br:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:14]2[CH2:15][CH2:16][CH2:17][CH2:18][C:13]=2[CH:12]=[N:10]1

Participants

4

Reactant 2

HCID 101871Cyclohexanone, 2-(hydroxymethylene)-HCID 27239122-Bromophenylhydrazine hydrochloride

Product 1

HCID 71253453HCID 71253453, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Bromophenylhydrazine hydrochloride (1.00 g, 4.47 mmol) was added to a solution of 2-(hydroxymethylene)cyclohexanone (0.564 g, 4.47 mmol) in ethanol (20 mL) and the resulting solution was refluxed 3 h before being concentrated. The crude material was taken up in DCM and washed with saturated ammonium chloride, 1N NaOH, saturated sodium chloride, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give 1-(2-bromophenyl)-4,5,6,7-tetrahydro-1H-indazole.

Workup

  1. temperaturethe resulting solution was refluxed 3 h
  2. concentrationbefore being concentrated
  3. washwashed with saturated ammonium chloride, 1N NaOH, saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-533b0c10b45c4331af854929507f2e56
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Linked notes

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