Reaktion #2473920

Reaktionsgleichung

methylglycolate

Sodium hydride

6-chloro-5-nitro-nicotinic acid ethyl ester

6-hydroxy-nicotinic acid

nitric acid

PCl5

POCl3

→

title compound

6-Methoxycarbonylmethoxy-5-nitro-nicotinic acid ethyl ester

Lösungsmittel

Water

dioxan

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture was extracted with EtOAc
2. 2
   TrocknenThe organic phase was dried (MgSO4)
3. 3
   Filtrationfiltered
4. 4
   Einengenconcentrated to dryness
5. 5
   SonstigeThe product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>7:3)

Vorschrift

To a solution of 6-chloro-5-nitro-nicotinic acid ethyl ester (10.5 g, prepared from 6-hydroxy-nicotinic acid with a) fuming nitric acid, b) PCl5, POCl3, c) EtOH, see WO2005012288) in dioxan (100 ml) was added methylglycolate (4.92 g). Sodium hydride (55% dispersion in mineral oil, 2.19 g) was added portion wise at 0° C. The mixture was stirred at room temperature for 24 h. Water was added and the mixture was extracted with EtOAc. The organic phase was dried (MgSO4), filtered and concentrated to dryness. The product was purified by chromatography (SiO2, cyclohexane/EtOAc 1:0=>7:3) to give the title compound (3.026 g) as yellow oil. MS (m/e)=285.2 [M+H+].

Quelle