반응 #162691

반응 방정식

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

용매

toluene

반응 조건

후처리

1. 1
   온도The reaction mixture was heated
2. 2
   온도at reflux for 20 h
3. 3
   기타The solvent was removed in vacuo
4. 4
   기타the residue was partitioned between 2M HCl and EtOAc
5. 5
   추출The organic extract
6. 6
   추출was extracted several times with 2M HCl
7. 7
   추출The acidic extract
8. 8
   추출then re-extracted 3× with EtOAc
9. 9
   건조The combined organic extracts were dried (MgSO4)
10. 10
    기타the solvent removed

실험 절차

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).

출처