Dicyclohexylcarbodiimide → HCID 10762413, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence