Reaktion #46531

Reaktionsgleichung

H2SO4

2-aminonicotinic acid

MeOH

→

title compound

Ausbeute 71.0%

Methyl 2-aminonicotinate

Ausbeute 71.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturat reflux
3. 3
   Sonstigea homogeneous solution formed within 5 min
4. 4
   Einengenconcentrated under vacuum
5. 5
   Extraktionextracted with EtOAc (500 mL)
6. 6
   WaschenThe organic layer was washed with brine
7. 7
   Trocknendried (Na2SO4)
8. 8
   Einengenconcentrated to dryness

Vorschrift

Concentrated H2SO4 (20 mL, 360 mmole) was added dropwise over 5 minutes to a suspension of 2-aminonicotinic acid (25 g, 181 mmole) in MeOH (400 mL), and the mixture was heated at reflux; a homogeneous solution formed within 5 min. After 72 h, the reaction was cooled to room temperature and concentrated under vacuum. The residue was basified with 1.0 N Na2CO3 (500 mL) (Gas evolution!) and extracted with EtOAc (500 mL). The organic layer was washed with brine, dried (Na2SO4), and concentrated to dryness to give the title compound (19.6 g, 71%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.22 (dd, 1 H), 8.13 (dd, 1 H), 6.63 (dd, 1 H), 6.30 (br s, 2 H), 3.89 (s, 3 H).

Quelle