Reaktion #157326

Reaktionsgleichung

HCl

potassium hydroxide

carbon disulfide

Ammonium formate

2-nitro-3-hydroxy-6-methylpyridine

→

5-Methyloxazolo[4,5-b]pyridine-2(3H)-thione

Lösungsmittel

EtOH

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to rt
2. 2
   Filtrationwas filtered through Celite®
3. 3
   EinengenThe filtrate was concentrated under reduced pressure
4. 4
   Sonstigeyielding a thick orangish oil
5. 5
   TemperaturThe reaction mixture was heated
6. 6
   Temperaturto reflux overnight
7. 7
   TemperaturUpon cooling to rt
8. 8
   Filtrationthe resulting solid was collected by filtration
9. 9
   WaschenThe solid was washed with water (2×) and air
10. 10
    Sonstigedried
11. 11
    Sonstigeby drying in a 35° C. vacuum oven

Vorschrift

Ammonium formate (1.64 g, 26 mmol) was added to a suspension of Pd(OH)2 on carbon (˜20% Pd, 0.73 g, 1.0 mmol) and 2-nitro-3-hydroxy-6-methylpyridine (2.0 g, 13 mmol) in EtOH (20 mL). The reaction mixture was heated to 70° C. for 1 h at which point the reaction mixture was allowed to cool to rt and was filtered through Celite®. The filtrate was concentrated under reduced pressure, yielding a thick orangish oil. The material was dissolved in EtOH (25 mL) and potassium hydroxide (0.875 g, 15.6 mmol) and carbon disulfide (15 mL) were added. The reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was acidified with 1 N HCl, and the resulting solid was collected by filtration. The solid was washed with water (2×) and air dried followed by drying in a 35° C. vacuum oven. LC-MS: RT=5.58 min, [M+H]+=167.0.

Quelle