Reaktion #738237

Reaktionsgleichung

DCC

3-amino-2-phenylquinoline-4-carboxylic acid

1-hydroxybenzotriazole

(S)-α-ethyl benzylamine

→

title compound

Ausbeute 78.2%

(S)-N-(α-ethylbenzyl)-3-amino-2-phenylquinoline-4-carboxamide

Ausbeute 78.2%

Lösungsmittel

CH2Cl2

—

7/3

THF CH3CN

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   Sonstigeat room temperature
4. 4
   Sonstigeovernight
5. 5
   SonstigeThe reaction mixture was evaporated in-vacuo
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   Filtrationthe solution filtered off
8. 8
   Waschenwashed with H2O, 20% citric acid, sat. sol. NaHCO3 and sat. sol. NaCl
9. 9
   SonstigeThe organic layer was separated
10. 10
    Sonstigedrive over Na2SO4 and evaporated in-vacuo to dryness
11. 11
    Sonstigeto obtain 2.4 g of the crude product
12. 12
    SonstigeThis was triturated with i-Pr2O
13. 13
    Sonstigerecrystallized with a 10:1 mixture of iPr2O/i-PrOH

Vorschrift

1.5 g (5.7 mmol) of 3-amino-2-phenylquinoline-4-carboxylic acid (CAS [36735-26-9]) were dissolved in 140 ml of a 7/3 mixture of THF/CH3CN; 1.5 g (11.1 mmol) of 1-hydroxybenzotriazole (HOBT) were added and 1.15 g (8.5 mmol) of (S)-α-ethyl benzylamine dissolved in 10 ml of CH2Cl2 were added dropwise. After cooling of the reaction mixture to 0° C., 1.4 g (6.7 mmol) of dicyclohexylcarbodiimmide (DCC) dissolved in 10 ml of CH2Cl2 were added dropwise. The solution was kept at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was evaporated in-vacuo, the residue was dissolved in CH2Cl2 and the solution filtered off, washed with H2O, 20% citric acid, sat. sol. NaHCO3 and sat. sol. NaCl. The organic layer was separated, drive over Na2SO4 and evaporated in-vacuo to dryness to obtain 2.4 g of the crude product. This was triturated with i-Pr2O, then recrystallized with a 10:1 mixture of iPr2O/i-PrOH to yield 1.7 g of the title compound.

Quelle