반응 #43792

반응 방정식

7-(benzyloxy)-6-methoxyquinolin-4(1H)-one

Cs2CO3

3,4-difluoronitrobenzene

→

product

수율 46.0%

7-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

수율 46.0%

용매

DMF

CH3CN

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was stirred at rt overnight
2. 2
   workup.ADDITIONa mixture of O- and N-alkylation products
3. 3
   농축It was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL)
4. 4
   workup.ADDITIONwere added to the residue, EtOAc layer
5. 5
   기타was separated
6. 6
   건조dried over MgSO4
7. 7
   농축concentrated in vacuo
8. 8
   기타The residue was purified by flash column chromatography on silica gel eluting with hexane

실험 절차

A mixture of 7-(benzyloxy)-6-methoxyquinolin-4(1H)-one (4.4 g, 15.6 mmol), Cs2CO3 (9.0 g) in DMF (40 mL) and CH3CN (40 mL) was stirred for 30 minutes at rt. To this mixture was added 3,4-difluoronitrobenzene (2.5 g, 15.7 mmol), and the reaction mixture was stirred at rt overnight. The reaction product was a mixture of O- and N-alkylation products. It was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL) were added to the residue, EtOAc layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexane:EtOAc:MeOH/800:200:40, and then 700:300:40 to obtain the desired O-alkylation product (3.0 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 8.73 (d, 1H, J=6.0 Hz), 8.29-8.26 (m, 2H), 8.08 (s, 1H), 7.60-7.35 (m, 7H), 6.67 (d, 1H, J=6.6 Hz), 5.42 (s, 2H), 4.10 (s, 3H); MS(ESI+) m/z 421.3 (M+H)+.

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