반응 #640618

반응 방정식

ethyl benzoylacetate

m-anisidine

HCl

dioxane

→

title compound

수율 22.0%

2-phenyl-4-hydroxy-7-methoxy-quinoline

수율 22.0%

용매

toluene

water

반응 조건

후처리

1. 1
   기타was collected in a Dean-Stark apparatus
2. 2
   workup.WAITThe reaction mixture was left
3. 3
   기타the solvent removed under vacuum
4. 4
   온도the mixture was heated for 2 h at 240° C
5. 5
   workup.WAITThe reaction mixture was then left
6. 6
   온도to cool to ambient temperature
7. 7
   workup.ADDITIONdichloromethane (55 mL) was added
8. 8
   기타leading to the precipitation of a yellow solid
9. 9
   여과the solid collected by filtration
10. 10
    세척rinsing the cake with a small amount of dichloromethane
11. 11
    기타The solid was transferred to a 100 mL round bottom flask
12. 12
    workup.STIRRINGstirred with dichloromethane (50 mL) for another 45 min at ambient temperature
13. 13
    여과After filtration
14. 14
    기타drying under high vacuum

실험 절차

To a solution of ethyl benzoylacetate (10.00 g, 52.0 mmol., 1 eq) and m-anisidine (7.05 g, 57.2 mmol., 1.1 eq) in toluene (85 mL) was added 4M HCl in dioxane (0.520 mL, 2.08 mmol., 0.04 eq) dropwise. The reaction mixture was refluxed for 15 hours while water was collected in a Dean-Stark apparatus. The reaction mixture was left to cool to ambient temperature and the solvent removed under vacuum. The residue was suspended in diphenyl ether (28 mL) and the mixture was heated for 2 h at 240° C. The reaction mixture was then left to cool to ambient temperature and dichloromethane (55 mL) was added, leading to the precipitation of a yellow solid. Stirring was continued at ambient temperature for a further 30 min and the solid collected by filtration, rinsing the cake with a small amount of dichloromethane. The solid was transferred to a 100 mL round bottom flask and stirred with dichloromethane (50 mL) for another 45 min at ambient temperature. After filtration and drying under high vacuum, 2.85 g (22%) of the title compound was isolated as a pale yellow solid. 1H NMR (250 MHz, DMSO-d6) δ ppm 11.54 (s, 1 H), 7.99 (d, J=8.91 Hz, 1 H), 7.73-7.90 (m, 2 H), 7.48-7.64 (m, 3 H), 7.20 (d, J=2.32 Hz, 1 H), 6.94 (dd, J=2.34, 8.97 Hz, 1 H), 6.26 (s, 1 H), 3.86 (s, 3 H). LC-MS: purity 98% (UV), tR 1.52 min, m/z [M+1]+ 252.10.

출처