تفاعل #220022

معادلة التفاعل

compound

3-Formyl-2-hydroxy-5-trifluoromethylpyridine

sodium formate

hydroxylamine hydrochloride

formic acid

→

desired product

3-Cyano-2-hydroxy-5-trifluoromethylpyridine

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةto reflux overnight
3. 3
   درجة الحرارةThe reaction mixture was cooled
4. 4
   workup.WAITto stand at room temperature for 7 d
5. 5
   استخلاصextracted with three portions of ethyl acetate
6. 6
   غسيلThe combined organic layers were washed sequentially with two portions of water, saturated aqueous sodium bicarbonate solution and brine
7. 7
   تجفيفdried over sodium sulfate
8. 8
   تركيزconcentrated in vacuo

الإجراء التجريبي

A mixture of the compound from Step B above (18 g, 95 mmol), sodium formate (7.1 g, 110 mmol), hydroxylamine hydrochloride (7.3 g, 110 mmol), and formic acid (150 mL) was stirred at room temperature for 2 h and then heated to reflux overnight. The reaction mixture was cooled, allowed to stand at room temperature for 7 d, poured into water and extracted with three portions of ethyl acetate. The combined organic layers were washed sequentially with two portions of water, saturated aqueous sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated in vacuo to yield the desired product as a brown powder. 1H NMR (400 MHz, CD3OD) δ 8.37 (d, J=2.7 Hz, 1H), 8.19 (q, J=0.7 Hz, 0.3 Hz, 1H).

المصدر