Reaktion #80240

Reaktionsgleichung

2-benzyloxy-3-methoxybenzoic acid

thionyl chloride

7-amino-quinoline-3-carboxylic acid (di-pyridin-2-yl-methyl)-amide

pyridine

→

title compound

Ausbeute 34.0%

7-(2-Benzyloxy-3-methoxy-benzoylamino)-quinoline-3-carboxylic acid (di-pyridin -2-yl-methyl)-amide

Ausbeute 34.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 2 hr
3. 3
   SonstigeThe thionyl chloride was removed in vacuo, with traces
4. 4
   Sonstigebeing removed
5. 5
   workup.ADDITIONby adding methylene chloride
6. 6
   Einengenconcentrating the solution in vacuo
7. 7
   workup.DISSOLUTIONThe resulting 2-benzyloxy-3-methoxybenzoyl chloride was dissolved in chloroform
8. 8
   TemperaturThe resulting solution was heated
9. 9
   Temperaturunder reflux for 3 hr
10. 10
    Einengenconcentrated to dryness in vacuo
11. 11
    workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
12. 12
    Waschenwashed sequentially with water and brine
13. 13
    Trocknendried over anhydrous sodium sulfate
14. 14
    Einengenconcentrated to dryness in vacuo
15. 15
    SonstigeThe residue (960 mg) was purified by column chromatography on silica gel
16. 16
    Wascheneluting with 98:2 chloroform/methanol

Vorschrift

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).

Quelle