Reaktion #170082

Reaktionsgleichung

water

water

Lithium aluminum hydride

2-amino-3-carboxypyridine

sodium

→

title product

2-Amino-3-(hydroxymethyl)pyridine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONOnce the addition
2. 2
   Temperaturat reflux overnight
3. 3
   FiltrationThe resulting white suspension was filtered on Clarcel®
4. 4
   Waschenthe cake was washed with THF (200 mL)
5. 5
   workup.ADDITIONa mixture of CHCl3/MeOH (250 mL, 9:1)
6. 6
   EinengenAfter concentration to dryness of the filtrate

Vorschrift

Lithium aluminum hydride (12.4 g, 326.7 mmol) was portionwisely added to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217.2 mmol) in THF (350 mL) at 0° C. Once the addition was completed, the reaction mixture was stirred at room temperature for 15 minutes and then at reflux overnight. The mixture was then cooled to 0° C. and hydrolyzed by the successive addition of water (18 mL), a solution of sodium hydroxyde (18 mL) and water (30 mL) again. The resulting white suspension was filtered on Clarcel® and the cake was washed with THF (200 mL) and a mixture of CHCl3/MeOH (250 mL, 9:1). After concentration to dryness of the filtrate, the title product was obtained as a yellow solid (24.2 g, 90%).

Quelle