Реакция #164573

Уравнение реакции

methyliodide

2-chloro-5-nitroisonicotinic acid

Intermediate 25A

2-chloro-5-nitroisonicotinic acid

sodium carbonate

→

methyl 2-chloro-5-nitroisonicotinate

Выход 90.2%

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеReaction
2. 2
   Температураcooled in an ice bath
3. 3
   workup.ADDITIONAfter complete addition, reaction
4. 4
   ФильтрацияThe reaction mixture was filtered
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe resultant crude material was purified by a 20 g silica column
7. 7
   Промывкаeluting with 40% ethylacetate in hexane

Методика

To a solution of 2-chloro-5-nitroisonicotinic acid (Intermediate 25A) (0.64 g, 3.17 mmol) in DMF (15 mL) under nitrogen was added sodium carbonate (1.0 g, 9.51 mmol). Reaction cooled in an ice bath and methyliodide (1.35 g, 9.51 mmol) was added dropwise. After complete addition, reaction allowed to warm to room temperature and stirred overnight under nitrogen. The reaction mixture was filtered and concentrated. The resultant crude material was purified by a 20 g silica column eluting with 40% ethylacetate in hexane to afford methyl 2-chloro-5-nitroisonicotinate (0.62 g, 2.86 mmol).

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