Reaktion #162691

Reaktionsgleichung

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

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturat reflux for 20 h
3. 3
   SonstigeThe solvent was removed in vacuo
4. 4
   Sonstigethe residue was partitioned between 2M HCl and EtOAc
5. 5
   ExtraktionThe organic extract
6. 6
   Extraktionwas extracted several times with 2M HCl
7. 7
   ExtraktionThe acidic extract
8. 8
   Extraktionthen re-extracted 3× with EtOAc
9. 9
   TrocknenThe combined organic extracts were dried (MgSO4)
10. 10
    Sonstigethe solvent removed

Vorschrift

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).

Quelle