1-Hydroxybenzotriazole → 3-Quinolinecarboxamide

Temperature

0 °C

To a mixture of 3-quinolinecarboxylic acid (3.32 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (3.37 g), N-hydroxybenzotriazole (2.6 g) and dichloromethane (50 ml) at 0° C. was added triethylamine (2.3 ml). After 15 minutes, a solution of 4-ethyl-2,4-hexadien-1-ylamine (2.0 g) in dichloromethane (10 ml) was added dropwise to the solution over a period of 10 minutes. The mixture was stirred at 0° C. for 30 minutes and then at room temperature overnight. The reaction mixture was diluted with aqueous sodium hydrogen carbonate. The separated organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on silica gel (1% methanol-chloroform) to give N-[(2E,4E)- and (2Z,4E)-4-ethyl-2,4-hexadien-1-yl]-3-quinolinecarboxamide (3.18 g) as an oil.

1. customat room temperature
2. customovernight
3. washThe separated organic phase was washed with water and brine
4. dry with materialdried over anhydrous magnesium sulfate
5. customevaporated in vacuo
6. customThe residue was chromatographed on silica gel (1% methanol-chloroform)

ORD record

ord-894db4f725824f9fb6d4513565532c6d

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05495023