تفاعل #2146685

معادلة التفاعل

2-bromo-3-methoxy-6-nitropyridine

hydrazine monohydrate

→

2-amino-5-methoxypyridine

المردود 88.3%

المذيبات

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAfter the reaction mixture was refluxed for 70 minutes
2. 2
   ترشيحThen, after palladium-carbon was filtered off
3. 3
   غسيلthe residue was washed with ethanol
4. 4
   تركيزThe 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
   استخلاصthe resulting mixture was extracted eight times with chloroform
7. 7
   تجفيفThe combined chloroform layer was dried over anhydrous sodium sulfate
8. 8
   تركيزconcentrated under reduced pressure
9. 9
   workup.DISTILLATIONThe resulting crude product was distilled under reduced pressure

الإجراء التجريبي

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).

المصدر