反応 #738237

反応方程式

DCC

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

1-hydroxybenzotriazole

(S)-α-ethyl benzylamine

→

title compound

収率 78.2%

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

収率 78.2%

溶媒

CH2Cl2

—

7/3

THF CH3CN

CH2Cl2

反応条件

後処理

1. 1
   workup.ADDITIONwere added dropwise
2. 2
   workup.ADDITIONwere added dropwise
3. 3
   その他at room temperature
4. 4
   その他overnight
5. 5
   その他The reaction mixture was evaporated in-vacuo
6. 6
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2
7. 7
   ろ過the solution filtered off
8. 8
   洗浄washed with H2O, 20% citric acid, sat. sol. NaHCO3 and sat. sol. NaCl
9. 9
   その他The organic layer was separated
10. 10
    その他drive over Na2SO4 and evaporated in-vacuo to dryness
11. 11
    その他to obtain 2.4 g of the crude product
12. 12
    その他This was triturated with i-Pr2O
13. 13
    その他recrystallized with a 10:1 mixture of iPr2O/i-PrOH

実験手順

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.

出典