Toluene → HCID 178423753, compound

HRID 1624039Notes

Reaction equation

HRID 1624039 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][C:3]1=O.[C:17]1(C)C=CC=CC=1.[NH2:24][NH2:25]>CO>[CH3:1][CH:2]1[C:7]2[C:6](=[CH:17][NH:24][N:25]=2)[CH:5]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 9321HydrazineHCID 71114821HCID 71114821, compound

Product 1

HCID 178423753HCID 178423753, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

(cis)-4-(4-Methyl-3-oxo-cyclohexyl)benzonitrile (0.55 g, 2.58 mmol) is added to toluene (10.0 mL) and tert-butoxybis(dimtheylamino)methane (0.67 mL, 3.22 mmol) and stirred at 120° C. for 16 hours. The mixture is cooled to room temperature and concentrated in vacuo. The residue is added to MeOH (10.0 mL) and hydrazine (0.07 mL, 2.32 mmol) and stirred at 80° C. for 1.0 hour. The mixture is cooled to room temperature and concentrated in vacuo. The residue is purified by silica gel chromatography (35%-55% EtOAc/hexanes) to give (+/−)-(cis/trans)-4-[7-methyl-4,5,6,7-tetrahydro-2H-indazol-4-yl]benzonitrile (0.360 g, 58%). ES/MS m/z 238 (M+H).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. stirringstirred at 80° C. for 1.0 hour
  4. temperatureThe mixture is cooled to room temperature
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography (35%-55% EtOAc/hexanes)

Sources & evidence

ORD record
ord-31fcc7d562054018a629c845123b841e
Source dataset
uspto-grants-2014_07
Patent number
US08778984B2

Reaction notes

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