反応 #2146685

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, after palladium-carbon was filtered off
3. 3
   洗浄the residue was washed with ethanol
4. 4
   濃縮The combined solution was concentrated under reduced pressure
5. 5
   workup.ADDITIONThen, 1300 mL of water and 130 mL of conc. aqueous ammonia were added to the concentrate
6. 6
   抽出the resulting mixture was extracted eight times with chloroform
7. 7
   乾燥The combined chloroform layer was dried over anhydrous sodium sulfate
8. 8
   濃縮concentrated under reduced pressure
9. 9
   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. To the mixture, 283 mL of hydrazine monohydrate was then added dropwise. After the reaction mixture was refluxed for 70 minutes, the reaction solution was cooled down to room temperature. Then, after palladium-carbon was filtered off, the residue was washed with ethanol, and the washings were combined with the filtrate. The combined solution was concentrated under reduced pressure. Then, 1300 mL of water and 130 mL of conc. aqueous ammonia were added to the concentrate, and the resulting mixture was 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. 2, Step 3).

出典