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

HRID 1696426Notes

Reaction equation

HRID 1696426 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([NH:10][NH2:11])[CH:7]=[CH:8][CH:9]=1.[C:12]([CH2:18][C:19]#[N:20])(=O)[C:13]([CH3:16])([CH3:15])[CH3:14]>C1(C)C=CC=CC=1>[C:13]([C:12]1[CH:18]=[C:19]([NH2:20])[N:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH3:2])[CH:5]=2)[N:11]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-HCID 27239403-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 109117983-tert-butyl-1-(3-methoxyphenyl)-1H-pyrazol-5-amineYield 90.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of commercially available 3-methoxyphenylhydrazine hydrochloride (1.0 g, 5.7 mmol) in toluene (5 mL) was added commercially available pivaloylacetonitrile (0.70 g, 5.5 mmol). The reaction mixture was heated at reflux for 5 h, filtered and washed with hexane to obtain 3-t-butyl-1-(3-methoxyphenyl)-1H-pyrazol-5-amine (1.22 g, 89% yield) as its hydrochloride salt as a pale yellow solid which was used without further purification. 1H NMR (300 MHz, CDCl3): δ 7.35 (t, J=8.4 Hz, 1H), 7.04 (t, J=2.1 Hz, 1H), 7.00 (dd, J=1.5 and 7.5 Hz, 1H), 6.95 (dd, J=2.1 and 8.4 Hz, 1H), 5.90 (brs, 2H), 5.83 (s, 1H), 3.81 (s, 3H), 1.89 (s, 9H); MS (EI) m/z: 246 (M+H+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 5 h
  3. filtrationfiltered
  4. washwashed with hexane

Sources & evidence

ORD record
ord-83e70e3c28e6431da7d13545ed86c471
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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