Ethanol → 3-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

HRID 1864524Notes

Reaction equation

HRID 1864524 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.[CH3:12][C:13]([CH3:20])([CH3:19])[C:14](=O)[CH2:15][C:16]#[N:17].CCO.C([O-])([O-])=O.[Na+].[Na+]>CCOCC.CC(O)=O>[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:16]([NH2:17])=[CH:15][C:14]([C:13]([CH3:20])([CH3:19])[CH3:12])=[N:11]2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 111393953-(tert-Butyl)-1-(4-methoxyphenyl)-1H-pyrazol-5-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4-methoxyphenylhydrazine hydrochloride (3.5 g), 4,4-dimethyl-3-oxopentanenitrile (2.5 g), EtOH (30 mL), and AcOH (1 mL) was heated at the reflux temperature for 3 h, cooled to room temp., and poured into a mixture of Et2O (100 mL) and a 10% Na2CO3 solution (100 mL). The organic layer was washed with a saturated NaCl solution, dried (MgSO4) and concentrated under reduced pressure. The solid residue was washed with pentane to afford the desired pyrazole as a pale brown solid. (4.25 g): 1H-NMR (DMSO-d6) δ 1.18 (s, 9H); 3.78 (s, 3H); 5.02 (br s, 2H); 5.34 (s, 1H); 6.99 (d, J=8 Hz, 2H); 7.42 (d, J=8 Hz, 2H).

Workup

  1. temperaturewas heated at the reflux temperature for 3 h
  2. temperaturecooled to room temp.
  3. washThe organic layer was washed with a saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washThe solid residue was washed with pentane

Sources & evidence

ORD record
ord-8994ae9b43fa446285479d911db47e0f
Source dataset
uspto-grants-2009_12
Patent number
US07625915B2

Reaction notes

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