Triethylamine → 6-Fluoro-7-methylisoquinolin-1(2H)-one

温度

2.5 °C

To a solution of 10.0 g (55.5 mmol) of 3-fluoro-4-methyl-cinnamic acid in 80 ml of acetone were subsequently added at 0° C. 6.74 g (66.6 mmol) of triethylamine in 10 ml of acetone followed by 7.83 g (72.2 mmol) of ethyl chloroformate. After stirring for 2 h at 0 to 5° C., a solution of 4.0 g (61.1 mmol) of sodium azide in 9.5 ml of water was added. After stirring for 1 additional h the reaction mixture was poured onto 200 ml of 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 another 1 h at 230-250° C. After cooling down to 150° C. the reaction mixture was poured into 270 ml of 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.

1. stirringAfter stirring for 1 additional h the reaction mixture
2. extractionextracted twice with chloroform
3. dry with materialThe organic phase was dried over magnesium sulfate, 40 ml diphenylether
4. additionwere added
5. customthe chloroform was cautiously removed in vacuo
6. additionThe residue was then added dropwise into 50 ml of diphenylether, which
7. customhad been preheated to 245° C
8. additionAfter complete addition it
9. stirringwas stirred for another 1 h at 230-250° C
10. temperatureAfter cooling down to 150° C. the reaction mixture
11. additionwas poured into 270 ml of heptane
12. temperatureafter further cooling in an ice bath the precipitated product
13. filtrationwas filtered by suction

ORDレコード

ord-68e54df07899492db4859a04a705c696

出典データセット

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08742116B2