Реакция #90212

Уравнение реакции

2-amino-3-methylbenzoic acid

N-chlorosuccinimide

→

desired intermediate

Выход 75.5%

2-amino-3-methyl-5-chlorobenzoic acid

Выход 75.5%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe heat was removed
2. 2
   Температураthe reaction was cooled to room temperature
3. 3
   workup.ADDITIONThe reaction mixture was then slowly poured into ice-water (250 mL)
4. 4
   Другоеto precipitate a white solid
5. 5
   ФильтрацияThe solid was filtered
6. 6
   Промывкаwashed four times with water
7. 7
   СушкаThe ethyl acetate solution was dried over magnesium sulfate
8. 8
   Другоеevaporated under reduced pressure
9. 9
   Промывкаthe residual solid was washed with ether

Методика

To a solution of 2-amino-3-methylbenzoic acid (Aldrich, 15.0 g, 99.2 mmol) in N,N-dimethylformamide (50 mL) was added N-chlorosuccinimide (13.3 g, 99.2 mmol) and the reaction mixture was heated to 100° C. for 30 minutes. The heat was removed, the reaction was cooled to room temperature and let stand overnight. The reaction mixture was then slowly poured into ice-water (250 mL) to precipitate a white solid. The solid was filtered and washed four times with water and then taken up in ethyl acetate (900 mL). The ethyl acetate solution was dried over magnesium sulfate, evaporated under reduced pressure and the residual solid was washed with ether to afford the desired intermediate as a white solid (13.9 g).

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