반응 #43787

반응 방정식

4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline

NH4Cl

DMF

water

→

product

수율 41.0%

4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorobenzenamine

수율 41.0%

용매

MeOH

THF

반응 조건

후처리

1. 1
   온도was heated
2. 2
   온도at reflux temp
3. 3
   workup.STIRRINGstirred for 10 minutes
4. 4
   여과the solid was filtered
5. 5
   농축The filtrate solution was concentrated in vacuo
6. 6
   기타the residue was purified by preparative HPLC

실험 절차

A mixture of 4-(2-fluoro-4-nitrophenoxy)-6,7-dimethoxyquinoline (612 mg, 1.8 mmol), Zn powder (2.0 g) and NH4Cl (1.4 g) in MeOH (25 mL) and THF (25 mL) was heated at reflux temp. overnight with stirring. To this mixture was added DMF (45 mL) and water (20 mL), stirred for 10 minutes, and the solid was filtered. The filtrate solution was concentrated in vacuo, and the residue was purified by preparative HPLC to afford the product (230 mg, 41%) as a brown solid. 1H NMR (CDCl3) δ 8.38 (d, 1H, J=5.5 Hz), 7.52 (s, 1H), 7.32 (s, 1H), 6.91 (t, 1H, J=8.8 Hz), 6.44 (dd, 1H, J=11.6, 2.2 Hz), 6.38 (dd, 1H, J=8.2, 2.2 Hz), 6.32 (d, 1H, J=5.0 Hz), 3.94 (s, 3H), 3.92 (s, 3H).

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