反应详情

To a solution of 5-chloro-8-hydroxy-2-methyl-7-quinolinecarboxylic acid (0.500 g) and 3-phenylpropylamine (0.33 mL) in 20 mL DMF is added EDC hydrochloride (0.444 g) and hydroxybenzotriazole hydrate (0.312 g). The reaction is stirred at room temperature for 48 h. The mixture is then partitioned between EtOAc and water. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine (1×), dried over sodium sulfate and condensed. The residue is stirred in 20 mL 1:1 THF/1N HCl overnight. The solution is neutralized with saturated aqueous NaHCO3. The reaction is partitioned between EtOAc and water. The aqueous layer is extracted with EtOAc (3×). The combined organic layers are washed with brine (1×), dried and condensed. The crude product is chromatographed on silica, eluting with 3% MeOH/CH2Cl2. Fractions homogeneous by TLC are combined and condensed. The residue taken up in a minimal amount of CH2Cl2. Toluene is added to the solution and the mixture is sonicated while adding hexanes until a white solid formed. The solid is collected and dried to yield 0.310 g of the title product as a white solid.

1. customThe mixture is then partitioned between EtOAc and water
2. extractionThe aqueous layer is extracted with EtOAc (3×)
3. washThe combined organic layers are washed with brine (1×)
4. dry with materialdried over sodium sulfate and condensed
5. stirringThe residue is stirred in 20 mL 1:1 THF/1N HCl overnight
6. customThe reaction is partitioned between EtOAc and water
7. extractionThe aqueous layer is extracted with EtOAc (3×)
8. washThe combined organic layers are washed with brine (1×)
9. customdried
10. customcondensed
11. customThe crude product is chromatographed on silica
12. washeluting with 3% MeOH/CH2Cl2
13. customcondensed
14. customthe mixture is sonicated
15. customformed
16. customThe solid is collected
17. customdried