反应详情

A mixture of 2-benzyloxy-3-methoxybenzoic acid (109 mg, 0.42 mmol), thionyl chloride (5 ml) and 1 drop dimethylformamide was heated under reflux for 2 hr. The thionyl chloride was removed in vacuo, with traces being removed by adding methylene chloride and concentrating the solution in vacuo. The resulting 2-benzyloxy-3-methoxybenzoyl chloride was dissolved in chloroform and the solution was added dropwise to a solution of 7-amino-quinoline-3-carboxylic acid (di-pyridin-2-yl-methyl)-amide (75 mg, 0.21 mmol), 4-(N,N-dimethylaminopyridine) (DIMAP) (3 mg, 0.02 mmol) and pyridine (0.068 ml, 0.84 mmol) in chloroform at room temperature. The resulting solution was heated under reflux for 3 hr, then cooled to room temperature and concentrated to dryness in vacuo. The residue was dissolved in ethyl acetate, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated to dryness in vacuo. The residue (960 mg) was purified by column chromatography on silica gel, eluting with 98:2 chloroform/methanol to yield the title compound as a solid (40.3 mg, 34% yield).

1. temperaturewas heated
2. temperatureunder reflux for 2 hr
3. customThe thionyl chloride was removed in vacuo, with traces
4. custombeing removed
5. additionby adding methylene chloride
6. concentrationconcentrating the solution in vacuo
7. dissolutionThe resulting 2-benzyloxy-3-methoxybenzoyl chloride was dissolved in chloroform
8. temperatureThe resulting solution was heated
9. temperatureunder reflux for 3 hr
10. concentrationconcentrated to dryness in vacuo
11. dissolutionThe residue was dissolved in ethyl acetate
12. washwashed sequentially with water and brine
13. dry with materialdried over anhydrous sodium sulfate
14. concentrationconcentrated to dryness in vacuo
15. customThe residue (960 mg) was purified by column chromatography on silica gel
16. washeluting with 98:2 chloroform/methanol