Reaktion #503783

Reaktionsgleichung

3-hydroxy-6-methyl-2-nitropyridine

H2O

sodium hydrosulfide hydrate

→

amine

Ausbeute 89.5%

2-amino-3-hydroxy-6-methylpyridine

Ausbeute 89.5%

Lösungsmittel

MeOH

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturunder reflux for 5 hours
2. 2
   Einengenconcentrated to dryness
3. 3
   workup.DISSOLUTIONThe resulting residue was dissolved in 300 mL of CH2Cl2
4. 4
   SonstigeThe mixture was sonicated for 10 min
5. 5
   SonstigeThe resulting salts that precipitated out at this point
6. 6
   Sonstigewere removed by filtration
7. 7
   EinengenThe filtrate was concentrated
8. 8
   Sonstigeto afford the crude amine
9. 9
   SonstigeThis was purified
10. 10
    Wascheneluting with 95% CH2Cl2, 4% MeOH and 1% Et3N

Vorschrift

7.00 g of 3-hydroxy-6-methyl-2-nitropyridine (Aldrich, 0.045 mol) was dissolved in 250 mL of MeOH and 20 mL of H2O along with 15 g of sodium hydrosulfide hydrate (6 eq, 0.27 mol). The reaction mixture was stirred under reflux for 5 hours. The reaction mixture was cooled to room temperature and diluted with 300 mL of absolute EtOH and concentrated to dryness. The resulting residue was dissolved in 300 mL of CH2Cl2 and 10 mL of MeOH. The mixture was sonicated for 10 min and allowed to stand at room temperature for 3 hours. The resulting salts that precipitated out at this point were removed by filtration. The filtrate was concentrated to afford the crude amine. This was purified by passing through a short plug of silica gel and eluting with 95% CH2Cl2, 4% MeOH and 1% Et3N. A total of 5.0 g of the desired amine was obtained (89% yield).

Quelle