Triethylamine → 3-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

HRID 1660992Notes

Reaction equation

HRID 1660992 reaction equation
Cl.[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][NH2:9].[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16].CCN(CC)CC>C1(C)C=CC=CC=1>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:10])[N:9]=1)([CH3:19])([CH3:18])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 71554o-Tolylhydrazinium(1+) chlorideHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 7706433-tert-Butyl-1-(2-methylphenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of o-tolyl-hydrazine hydrochloride (0.3 mmol) in 0.5 mL of toluene with 4,4-dimethyl-3-oxopentanenitrile (375 mg, 3 mmol, 10 equiv) and Et3N (84 μL, 0.6 mmol, 2 equiv) is stirred at 110° C. overnight. The solvent is evaporated and the residue taken up in EtOAC and washed with saturated NaHCO3 and brine. The organic layer is then concentrated and the residue diluted in 1 mL of ethanol and 1 mL of 1M HCl. The mixture was left at rt for 15 min and then it was concentrated. 5-tert-Butyl-2-o-tolyl-2H-pyrazol-3-ylamine is used crude in the preparation of Example 34.

Workup

  1. customThe solvent is evaporated
  2. washwashed with saturated NaHCO3 and brine
  3. concentrationThe organic layer is then concentrated
  4. additionthe residue diluted in 1 mL of ethanol
  5. concentrationit was concentrated
  6. customin the preparation of Example 34

Sources & evidence

ORD record
ord-029fa4004b3140268b35cda2ef716150
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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