반응 #80248

반응 방정식

Benzophenone imine

7-Chloro-quinoline-3-carboxylic acid ethyl ester

sodium t-butoxide

2-(dicylcohexylphosphino)biphenyl

→

7-(benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester

수율 12.3%

용매

toluene

ethyl acetate

반응 조건

후처리

1. 1
   기타The flask was flushed with nitrogen
2. 2
   기타The flask was fitted with a reflux condenser
3. 3
   온도The reaction mixture was cooled to room temperature
4. 4
   세척The reaction mixture was washed with a saturated sodium bicarbonate solution (25 mL), saturated ammonium chloride solution (25 mL), and brine (25 mL)
5. 5
   건조The organic layer was dried over sodium sulfate
6. 6
   workup.ADDITIONtreated with activated charcoal (Darco G-60®) (1 g)
7. 7
   여과The mixture was filtered through diatomaceous earth
8. 8
   농축concentrated

실험 절차

7-Chloro-quinoline-3-carboxylic acid ethyl ester (1 g, 4.24 mmol, 1 equiv), dry sodium t-butoxide (571 mg, 5.94 mmol, 1.4 equiv), tris(dibenzylideneacetone)dipalladium (19.5 mg, 21.2 μmol, 1 mol % equiv), and 2-(dicylcohexylphosphino)biphenyl (30 mg, 84.8 μmol, 4 mol % equiv) were placed in a round bottom flask with a magnetic stir bar. The flask was flushed with nitrogen. Benzophenone imine (783 μL, 4.66 mmol, 1.1 equiv) and toluene (8.5 mL) were added. The flask was fitted with a reflux condenser and the reaction was heated at 100° C. for 12 hours. The reaction mixture was cooled to room temperature and diluted with ethyl acetate (20 mL). The reaction mixture was washed with a saturated sodium bicarbonate solution (25 mL), saturated ammonium chloride solution (25 mL), and brine (25 mL). The organic layer was dried over sodium sulfate and then treated with activated charcoal (Darco G-60®) (1 g). The mixture was filtered through diatomaceous earth and concentrated. The residue was stirred in a minimal amount of isopropanol (about 2 mL) to provide 7-(benzhydrylidene-amino)-quinoline-3-carboxylic acid ethyl ester (199 mg, 12%) as a pale yellow solid.

출처