4-Methylphenylhydrazine monohydrochloride → 3-(1-(Benzyloxy)-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-amine

HRID 2069118Notes

Reaction equation

HRID 2069118 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.[CH2:11]([O:18][CH2:19][C:20]([CH3:27])([CH3:26])[C:21](=O)[CH2:22][C:23]#[N:24])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([O-])(O)=O.[Na+]>CCO>[CH2:11]([O:18][CH2:19][C:20]([C:21]1[CH:22]=[C:23]([NH2:24])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:10])=[CH:3][CH:4]=2)[N:9]=1)([CH3:26])[CH3:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 516892Sodium BicarbonateHCID 585647415-(Benzyloxy)-4,4-dimethyl-3-oxopentanenitrile

Product 1

HCID 674237623-(1-(Benzyloxy)-2-methylpropan-2-yl)-1-p-tolyl-1H-pyrazol-5-amineYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of p-tolylhydrazine hydrochloride (1.99 g, 12.6 mmol) and 5-(benzyloxy)-4,4-dimethyl-3-oxopentanenitrile (4.00 g, 13.8 mmol, 80% purity) in EtOH was heated at reflux for 16 hr and then cooled to RT. The mixture was neutralized with saturated aqueous NaHCO3 solution and extracted with EtOAc. The organic extracts were washed with brine, dried (MgSO4) and evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, 80 g, MeOH in DCM, 0-5%, gradient elution) to afford the title compound, (2.62 g, 60%); Rt 3.05 min (Method 1 basic); m/z 336 (M+H)+ (ES+).

Workup

  1. temperatureat reflux for 16 hr
  2. extractionextracted with EtOAc
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customThe residue was purified by flash column chromatography (SiO2, 80 g, MeOH in DCM, 0-5%, gradient elution)

Sources & evidence

ORD record
ord-c641257503ad4bb780cb830fed514eca
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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