反应详情

Dissolve N-(4-bromo-3-chloro-2-methyl-phenyl)-acetamide (10 g, 38 mmol) in N-methylpyrrolidinone (60 mL) and sparge with nitrogen. Add copper cyanide (10.2 g, 114 mol) and copper iodide (21.8 g, 114 mol) and stir under nitrogen at 130° C. for 72 h. Cool the reaction and add ethylene diamine (100 mL), along with water (300 mL). Extract the reaction mixture with EtOAc. Separate and dry the organic portion over Na2SO4, filter, and concentrate. Dissolve the resulting residue in 1:1 EtOH/concentrated HCl. Stir at reflux temperature for 30 min, cool and concentrate to half of the volume. Add water (500 mL) and filter. Rinse the filter cake with water and isolate 5.0 g (79%) of the title compound as a white solid. MS: MS (ESI−): 207 (M−1)−. MS (ESI+): 209 (M+1)+.

1. customsparge with nitrogen
2. temperatureCool
3. customthe reaction
4. extractionExtract the reaction mixture with EtOAc
5. customSeparate
6. dry with materialdry the organic portion over Na2SO4
7. filtrationfilter
8. concentrationconcentrate
9. dissolutionDissolve the resulting residue in 1:1 EtOH/concentrated HCl
10. temperatureat reflux temperature for 30 min
11. temperaturecool
12. concentrationconcentrate to half of the volume
13. filtrationAdd water (500 mL) and filter
14. washRinse the filter cake with water