反応 #2146705

反応方程式

2-bromo-3-methoxy-6-nitropyridine

hydrazine monohydrate

→

2-amino-5-methoxypyridine

収率 88.3%

溶媒

ethanol

反応条件

後処理

1. 1
   温度After the reaction mixture was refluxed for 70 minutes
2. 2
   ろ過Then, palladium-carbon was filtered off
3. 3
   洗浄which was then washed with ethanol
4. 4
   濃縮After the resulting solution was concentrated under reduced pressure
5. 5
   抽出extracted eight times with chloroform
6. 6
   乾燥The combined chloroform layer was dried over anhydrous sodium sulfate
7. 7
   濃縮concentrated under reduced pressure
8. 8
   workup.DISTILLATIONThe resulting crude product was distilled under reduced pressure

実験手順

55.6 g (corresponding to 0.239 mol) of 2-bromo-3-methoxy-6-nitropyridine was dissolved in 1700 mL of ethanol, and 37.3 g (50% wet) of 10% palladium-carbon was added thereto under argon stream. Then, 283 mL of hydrazine monohydrate was added dropwise. After the reaction mixture was refluxed for 70 minutes, the reaction solution was cooled down to room temperature. Then, palladium-carbon was filtered off, which was then washed with ethanol. The washings were combined with the filtrate. After the resulting solution was concentrated under reduced pressure, the concentrate was supplemented with 1300 mL of water and 130 mL of conc. aqueous ammonia, and extracted eight times with chloroform. The combined chloroform layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resulting crude product was distilled under reduced pressure, to obtain 26.2 g (corresponding to 0.211 mol) of 2-amino-5-methoxypyridine (FIG. 1, Step 3).

出典