Реакция #62030

Уравнение реакции

methyl iodide

2-amino-3-methylbenzoic acid

cesium carbonate

→

methyl 2-amino-3-methylbenzoate

Выход 92.3%

Растворители

N,N-dimethylformamide

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was partitioned between water (1 L) and ether (200 mL)
2. 2
   Экстракцияthe water layer was extracted with an additional volume of ether (100 mL)
3. 3
   ПромывкаThe combined extracts were washed with brine (500 mL)
4. 4
   Сушкаdried over anhydrous potassium carbonate
5. 5
   Концентрированиеconcentrated

Методика

To a solution of 2-amino-3-methylbenzoic acid (10.1 g, 66.9 mmol) in N,N-dimethylformamide (200 mL) was added cesium carbonate (33.2 g, 102 mmol, 1.5 eq). The mixture was stirred for 30 min. A solution of methyl iodide (4.17 mL, 67.0 mmol, 1.0 eq) in N,N-dimethylformamide (50 mL) was added dropwise and the reaction mixture was maintained for 18 h at rt. The reaction mixture was partitioned between water (1 L) and ether (200 mL) and the water layer was extracted with an additional volume of ether (100 mL). The combined extracts were washed with brine (500 mL), dried over anhydrous potassium carbonate, and concentrated to provide 10.2 g (92%) of methyl 2-amino-3-methylbenzoate. 1H NMR (400 MHz, CDCl3) δ 7.77 (d, 1H), 7.19 (d, 1H), 6.59 (t, 1H), 5.82 (bs, 2H), 3.86 (s, 3H), 2.17 (s, 3H).

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