Reacción #162691

Ecuación de reacción

Acetic acid

2-(2-chloro-4-methoxyphenyl)-3-oxobutanenitrile

hydrazine hydrate

→

title compound

4-(2-Chloro-4-methoxy-phenyl)-5-methyl-1H-pyrazol-3-ylamine

Disolventes

toluene

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was heated
2. 2
   Temperaturaat reflux for 20 h
3. 3
   OtroThe solvent was removed in vacuo
4. 4
   Otrothe residue was partitioned between 2M HCl and EtOAc
5. 5
   ExtracciónThe organic extract
6. 6
   Extracciónwas extracted several times with 2M HCl
7. 7
   ExtracciónThe acidic extract
8. 8
   Extracciónthen re-extracted 3× with EtOAc
9. 9
   SecadoThe combined organic extracts were dried (MgSO4)
10. 10
    Otrothe solvent removed

Procedimiento

Acetic acid (1.3 ml, 22.36 mmol) was added to a stirred suspension of 2-(2-chloro-4-methoxyphenyl)-3-oxobutanenitrile (2.0 g, 8.94 mmol) and hydrazine hydrate (0.65 ml, 13.41 mmol) in dry toluene (25 ml). The reaction mixture was heated at reflux for 20 h. The solvent was removed in vacuo and the residue was partitioned between 2M HCl and EtOAc. The organic extract was extracted several times with 2M HCl then discarded. The acidic extract was neutralised with NaHCO3 then re-extracted 3× with EtOAc. The combined organic extracts were dried (MgSO4) and the solvent removed to give the title compound as a viscous gum. No further purification was carried out; LCMS: Rt 1.19 mins; [M+H]+ 238.1 1H NMR (400 MHz, d6-DMSO) δ 1.95 (3H, s), 3.80 (3H, s), 4.1 (2H, br m), 6.92 (1H, s), 7.10 (1H, s), 7.20 (1H, d).

Fuente