反応 #607455

反応方程式

HCl

2-Furoyl chloride

3,4-diaminoquinoline

dichloromethane

Water

→

2-Furyl-1H-Imidazo[4,5-c]quinoline

溶媒

pyridine

NaOH

反応条件

後処理

1. 1
   その他to quench
2. 2
   その他the reaction
3. 3
   その他the solvent was evaporated under reduced pressure
4. 4
   その他to afford an orange solid
5. 5
   温度After cooling on ice the pH
6. 6
   その他The solid that precipitated
7. 7
   ろ過was filtered off
8. 8
   洗浄washed with water and ether
9. 9
   抽出Then extracted with ethyl acetate (3 times 15 ml)
10. 10
    洗浄washed with water (3 time 15 ml)
11. 11
    乾燥dried over MgSO4
12. 12
    その他The solvent was evaporated
13. 13
    その他the residue was dried

実験手順

2-Furoyl chloride (1.1 g, 0.8 ml, 8.1 mmol) in dry dichloromethane (15 ml) was added dropwise to a solution of to 3,4-diaminoquinoline 8 (1.0 g, 6.0 mmol) in dry pyridine (6.2 ml) under nitrogen. The solution was stirred for 2 hours at room temperature. Water (15 ml) was added to quench the reaction and the solvent was evaporated under reduced pressure to afford an orange solid. This crude solid in 2N NaOH (15 ml) was refluxed for 2 hours. After cooling on ice the pH was adjusted to 7 using concentrated HCl. The solid that precipitated was filtered off and washed with water and ether. Then extracted with ethyl acetate (3 times 15 ml) and washed with water (3 time 15 ml) and dried over MgSO4. The solvent was evaporated and the residue was dried. Eluent for column chromatography was 1-5% methanol in dichloromethane. Yield: 0.62 g (44%). Mp.: 236-238° C. 1H NMR (DMSO-d6): δ 6.74 (s, 1H, Ar); 7.35 (d, 1H, J=3.7 Hz, Ar); 7.69-7.73 (m, 2H, Ar); 7.83 (s, 1H, Ar); 8.09 (s, 1H, Ar); 8.46 (s, 1H, Ar); 9.09 (s, 1H, Ar). 13C NMR (DMSO-d6): δ 111.4, 112.6, 120.7, 121.8, 126.5, 127.2, 129.5, 138.2, 143.6, 144.3, 145.1, 147.2, 155.4.

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