Реакция #80195

Уравнение реакции

7-amino-quinoline-3-carboxylic acid ethyl ester

pyridine

2-(4-Trifluoromethyl-phenyl)-nicotinic acid

oxalyl chloride

→

brown gum

Выход 122.5%

7-{[2-(4-Trifluoromethyl-phenyl)-pyridine-3-carbonyl]-amino}-quinoline-3-carboxylic acid ethyl ester

Выход 122.5%

Растворители

dichloromethane

chloroform

dimethylformamide

dichloromethane

Условия реакции

Обработка

1. 1
   Другоеthe volatiles were removed under vacuum
2. 2
   ТемператураAfter heating
3. 3
   Температураat reflux overnight
4. 4
   Промывкаwashed with 35 ml of 2N NaOH, water
5. 5
   Сушкаdried (magnesium sulfate)
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated under vacuum

Методика

2-(4-Trifluoromethyl-phenyl)-nicotinic acid (534 mg, 2.0 mmol) was suspended in 10 ml of dichloromethane, and oxalyl chloride (0.7 ml, 8.0 mmol) was added followed by a drop of dimethylformamide. After 2 h at room temperature, the volatiles were removed under vacuum, and to the residue was added 10 ml of chloroform, 7-amino-quinoline-3-carboxylic acid ethyl ester (216 mg, 1.0 mmol), pyridine (0.2 ml, 2.5 mmol) and 4-dimethylaminopyridine (12 mg, 0.1 mmol). After heating at reflux overnight, the reaction mixture was diluted with 50 ml of dichloromethane, washed with 35 ml of 2N NaOH, water, dried (magnesium sulfate) filtered, and concentrated under vacuum to afford 570 mg of a brown gum. This material was purified by silica gel chromatography eluting with 50 to 80% ethyl acetate in hexanes to provide 189 mg of the title compound as a light yellow solid.

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