Reaktion #738236

Reaktionsgleichung

3-hydroxy-2-phenylquinoline-4-carboxylic acid

dicyclohexylcarbodiimide

1-hydroxybenzotriazole

(S)-α-ethylbenzylamine

→

title compound

Ausbeute 48.7%

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

Ausbeute 48.7%

Lösungsmittel

—

7/3

THF

CH2Cl2

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   workup.WAITThe reaction was left at room temperature overnight
4. 4
   Sonstigequenched with 20 ml of H2O
5. 5
   Sonstigeevaporated in-vacuo to dryness
6. 6
   workup.DISSOLUTIONdissolved in EtOAc
7. 7
   FiltrationThe precipitated dicyclohexylurea was filtered off
8. 8
   Waschenthe organic layer was washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl
9. 9
   SonstigeThe organic layer was separated
10. 10
    Trocknendried over Na2SO4
11. 11
    Sonstigeevaporated in-vacuo to dryness
12. 12
    Sonstigethe residue was purified by gradient column chromatography on 60-240 mesh silica gel using
13. 13
    workup.ADDITIONa mixture of hexane/EtOAc 9:1
14. 14
    workup.ADDITIONa mixture of hexane/EtOAc 7:3 as final eluent
15. 15
    SonstigeThe crude product was recrystallized from i-PrOH

Vorschrift

2.49 g (9.4 mmol) of 3-hydroxy-2-phenylquinoline-4-carboxylic acid (CAS [485-89-2]) were suspended in 150 ml of a 7/3 mixture of THF/CH3CH; 1.40 g (10.3 mmol) of 1-hydroxybenzotriazole (HOBT) and 1.27 g (9.4 mmol) of (S)-α-ethylbenzylamine dissolved in 20 ml of CH2Cl2 were added and the reaction mixture was stirred at room temperature for 30 minutes. 2.13 g (10.3 mmol) of dicyclohexylcarbodiimide (DCC) dissolved in 20 ml of CH2Cl2 were added dropwise. The reaction was left at room temperature overnight, quenched with 20 ml of H2O, evaporated in-vacuo to dryness and dissolved in EtOAc. The precipitated dicyclohexylurea was filtered off and the organic layer was washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl. The organic layer was separated, dried over Na2SO4 and evaporated in-vacuo to dryness; the residue was purified by gradient column chromatography on 60-240 mesh silica gel using a mixture of hexane/EtOAc 9:1 as starting eluent and a mixture of hexane/EtOAc 7:3 as final eluent. The crude product was recrystallized from i-PrOH to yield 1.75 g of the title compound as a white solid.

Quelle