反応 #162691

反応方程式

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

溶媒

toluene

反応条件

後処理

1. 1
   温度The reaction mixture was heated
2. 2
   温度at reflux for 20 h
3. 3
   その他The solvent was removed in vacuo
4. 4
   その他the residue was partitioned between 2M HCl and EtOAc
5. 5
   抽出The organic extract
6. 6
   抽出was extracted several times with 2M HCl
7. 7
   抽出The acidic extract
8. 8
   抽出then re-extracted 3× with EtOAc
9. 9
   乾燥The combined organic extracts were dried (MgSO4)
10. 10
    その他the solvent removed

実験手順

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).

出典