Reaktion #5111

Reaktionsgleichung

4-methoxyphenylhydrazine hydrochloride

Compound 29

4,6-Dioxo-6-(3-pyridyl)hexanoic acid

Et3N

→

title compound 31

Ausbeute 52.0%

3-[1-(4-Methoxyphenyl)-5-(3-pyridyl)-3-pyrazolyl]-propionic acid hydrochloride

Ausbeute 52.0%

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   Sonstigethe residue was partitioned between 5% NaOH and Et2O
3. 3
   SonstigeThe basic aqueous layer was separated
4. 4
   workup.ADDITIONSaturated brine was added
5. 5
   Extraktionthe aqueous layer was exhaustively extracted with CH2Cl2
6. 6
   EinengenThe combined CH2Cl2 layers were concentrated

Vorschrift

Compound 29 (2.21 g, 10 mM) in methanol (150 ml) containing Et3N (2 ml) was treated with 4-methoxyphenylhydrazine hydrochloride (1.85 g, 10.6 mM) at RT for 4 hr. The solvent was removed in vacuo and the residue was partitioned between 5% NaOH and Et2O. The basic aqueous layer was separated and acidified with 10% HCl to pH 2. Saturated brine was added and the aqueous layer was exhaustively extracted with CH2Cl2. The combined CH2Cl2 layers were concentrated to give the title compound 31 as a tan crystalline solid (Recry. Acetone, 1.87 g, 52%) mp=226°-228° C., MS, m/e 323 (M+).

Quelle