반응 #2146690

반응 방정식

2-bromo-3-methoxy-6-nitropyridine

hydrazine monohydrate

→

2-amino-5-methoxypyridine

수율 88.0%

용매

ethanol

반응 조건

후처리

1. 1
   온도After the reaction mixture was refluxed for 45 minutes
2. 2
   여과Then, after palladium-carbon was filtered off
3. 3
   세척the residue was washed with ethanol
4. 4
   농축The combined solution was concentrated under reduced pressure
5. 5
   workup.ADDITIONThen, 402 mL of water and 38 mL of conc. aqueous ammonia were added to the concentrate
6. 6
   추출the resulting mixture was extracted eight times with chloroform
7. 7
   건조The combined chloroform layer was dried over anhydrous sodium sulfate
8. 8
   농축concentrated under reduced pressure
9. 9
   workup.DISTILLATIONThe resulting crude product was distilled under reduced pressure

실험 절차

17.36 g (corresponding to 74.50 mmol) of 2-bromo-3-methoxy-6-nitropyridine was dissolved in 520 mL of ethanol, and 11.63 g (50% wet) of 10% palladium-carbon was added thereto under argon stream. To the mixture, 88.4 mL of hydrazine monohydrate was added dropwise. After the reaction mixture was refluxed for 45 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, 402 mL of water and 38 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 8.14 g (corresponding to 65.57 mmol) of 2-amino-5-methoxypyridine (FIG. 3, Step 3).

출처