4-Methylphenylhydrazine monohydrochloride → 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amine

HRID 1918052Notes

Reaction equation

HRID 1918052 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:11]1([CH3:19])[CH:16]=[CH:15][C:14]([NH:17][NH2:18])=[CH:13][CH:12]=1>CCO>[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:19])=[CH:12][CH:13]=2)[N:18]=1)([CH3:9])([CH3:8])[CH3:1]

Participants

4

Reactant 2

HCID 125044-Methylphenylhydrazine monohydrochlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 29741323-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-amineYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4,4-dimethyl-3-oxopentanenitrile (2.503 g, 20 mmol) and p-tolylhydrazine hydrochloride (3.173 g, 20 mmol) in EtOH was heated at 90° C. for 8 hours. The reaction was quenched by adding water and extracted with DCM. Extracts were dried over MgSO4 and concentrated to give 3-tert-butyl-1-p-tolyl-1H-pyrazol-5-amine as solid (4.537 g, 99%). 1H NMR (300 MHz, CDCl3) 1.31 (s, 9H), 2.36 (s, 3H), 3.69 (s, 2H), 5.51 (s, 1H), 7.25 (d, 2H), 7.44 (d, 2H); LC-MS (ESI) m/z 230 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. additionby adding water
  3. extractionextracted with DCM
  4. dry with materialExtracts were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-aa4ca1143cb34665ae06dd0fe1284e58
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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