Reaktion #170085

Reaktionsgleichung

water

lithium aluminum hydride

2-amino-3-carboxypyridine

sodium hydroxide

water

→

title product

2-Amino-3-(hydroxymethyl)pyridine

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONOnce the addition
2. 2
   Temperaturat reflux overnight
3. 3
   workup.STIRRINGThe resulting white suspension was stirred for one hour
4. 4
   Filtrationfiltered over Celite®
5. 5
   Waschenthe cake was washed with THF (400 mL)
6. 6
   EinengenAfter concentration to dryness of the filtrate

Vorschrift

A solution of 2.4M lithium aluminum hydride in THF (181 mL g, 434 mmol) was added portionwise to a suspension of 2-amino-3-carboxypyridine (30.0 g, 217 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 1M solution of sodium hydroxide (18 mL) and water (50 mL). The resulting white suspension was stirred for one hour, filtered over Celite® and the cake was washed with THF (400 mL). After concentration to dryness of the filtrate, the title product was obtained as a light brown oil (25.1 g, 87%, py 93.1%).

Quelle