Реакция #163119

Уравнение реакции

6-fluoronicotinic acid

N,O-Dimethylhydroxylamine hydrochloride

N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride

triethylamine

→

title compound

6-Fluoro-N-methoxy-N-methylnicotinamide

Растворители

DCM

Условия реакции

Обработка

1. 1
   ДругоеThe reaction was partitioned with water, layers
2. 2
   Сушкаorganic layer was dried over Na2SO4
3. 3
   Фильтрацияfiltered
4. 4
   Концентрированиеconcentrated in vacuo
5. 5
   ДругоеThe crude residue obtained
6. 6
   Фильтрацияwas purified by a silica gel filtration
7. 7
   Другоеto give

Методика

To a solution of 6-fluoronicotinic acid (10 g, 70.9 mmol) in DCM (200 ml), was added N,O-Dimethylhydroxylamine hydrochloride (7.3 g, 74.8 mmol), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (15 g, 78.5 mmol), and triethylamine (22 ml, 156 mmol). The reaction mixture was allowed to stir at room temperature for 16 hours. The reaction was partitioned with water, layers were cut, and organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue obtained was purified by a silica gel filtration using EtOAc-DCM (4:1) to give 7.2 g (55% isolated yield) of the title compound. 1H NMR: 8.48 (s, 1H) 8.21 (t, J=8.29 Hz, 1H) 7.27 (dd, J=8.29, 3.01 Hz, 1H) 3.54 (s, 3H) 3.27 (s, 3H).

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