Реакция #2146769

Уравнение реакции

sodium azide

3-fluoro-4-methyl-cinnamic acid

triethylamine

ethyl chloroformate

→

6-fluoro-7-methyl-2H-isoquinolin-1-one

Выход 41.7%

Растворители

water

acetone

acetone

Условия реакции

Обработка

1. 1
   workup.ADDITIONwas added
2. 2
   Экстракцияextracted twice with chloroform
3. 3
   СушкаThe organic phase was dried over magnesium sulfate, 40 ml diphenylether
4. 4
   workup.ADDITIONwere added
5. 5
   Другоеthe chloroform was cautiously removed in vacuo
6. 6
   workup.ADDITIONThe residue was then added dropwise into 50 ml of diphenylether which
7. 7
   Другоеhad been preheated to 245° C
8. 8
   workup.ADDITIONAfter complete addition it
9. 9
   workup.STIRRINGwas stirred for 1 further h at 230-250° C
10. 10
    workup.ADDITIONwas poured into 270 ml heptane
11. 11
    Температураafter further cooling in an ice bath the precipitated product
12. 12
    Фильтрацияwas filtered by suction

Методика

To a solution of 10.0 g (55.5 mmol) of 3-fluoro-4-methyl-cinnamic acid in 80 ml acetone were subsequently added at 0° C. 6.74 g (66.6 mmol) triethylamine in 10 ml acetone followed by 7.83 g (72.2 mmol) ethyl chloroformate. After stirring for 2 h at 0 to 5° C. a solution of 4.0 g (61.1 mmol) sodium azide in 9.5 ml water was added. After stirring for 1 additional h the reaction mixture was poured onto 200 ml ice water and extracted twice with chloroform. The organic phase was dried over magnesium sulfate, 40 ml diphenylether were added and the chloroform was cautiously removed in vacuo. The residue was then added dropwise into 50 ml of diphenylether which had been preheated to 245° C. After complete addition it was stirred for 1 further h at 230-250° C. After cooling down to 150° C. the reaction mixture was poured into 270 ml heptane and after further cooling in an ice bath the precipitated product was filtered by suction and 4.1 g 6-fluoro-7-methyl-2H-isoquinolin-1-one were obtained.

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