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-quinoline-carboxamide (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-e70a9573d3de4646a3a403367792c705

Source dataset

uspto-grants-1997_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05691366