Pentanenitrile, 4,4-dimethyl-3-oxo- → 3-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amine

HRID 711142Notes

Reaction equation

HRID 711142 reaction equation
Cl.[CH3:2][C:3]1[CH:4]=[C:5]([NH:10][NH2:11])[CH:6]=[CH:7][C:8]=1[CH3:9].[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17]>CCO>[C:13]([C:14]1[CH:15]=[C:16]([NH2:17])[N:10]([C:5]2[CH:6]=[CH:7][C:8]([CH3:9])=[C:3]([CH3:2])[CH:4]=2)[N:11]=1)([CH3:20])([CH3:19])[CH3:12]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 1737401-(3,4-Dimethylphenyl)hydrazine hydrochloride

Product 1

HCID 108685003-tert-Butyl-1-(3,4-dimethylphenyl)-1H-pyrazol-5-amineYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A black solution of 3,4-dimethylphenyl hydrazine hydrochloride (Apollo, 1.73 g, 10.0 mmol) and 4,4-dimethyl-3-oxopentanenitrile (1.38 g, 11.0 mmol) in EtOH (20 mL) was stirred at reflux for 5 h. The cooled solution was concentrated in vacuo, redissolved in diethyl ether (20 mL) and washed with aqueous NaOH solution (1M, 20 mL). The aqueous was extracted with diethyl ether (2×20 mL), then the combined organics washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo to leave the title compound (2.18 g, 90%). LCMS (Method 3): Rt 2.75 min, m/z 244 [MH+].

Workup

  1. temperatureat reflux for 5 h
  2. concentrationThe cooled solution was concentrated in vacuo
  3. dissolutionredissolved in diethyl ether (20 mL)
  4. washwashed with aqueous NaOH solution (1M, 20 mL)
  5. extractionThe aqueous was extracted with diethyl ether (2×20 mL)
  6. washthe combined organics washed with brine (20 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e63ab602d1a242a1b19278d90862f38c
Source dataset
uspto-grants-2015_11
Patent number
US09181242B2

Reaction notes

Loading…