Реакция #4664

ord-7771b7d4dfd64e73b2d9da266949289a

Уравнение реакции

CCOC(=O)c1cn(NC=O)c2cc(-n3cccc3)c(F)cc2c1=O
ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCI
ethyl iodide
CCOC(=O)c1cn(NC(C)C=O)c2cc(-n3cccc3)c(F)cc2c1=O
solid
Выход 37.7%
CCOC(=O)c1cn(NC(C)C=O)c2cc(-n3cccc3)c(F)cc2c1=O
ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylethylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate
Выход 37.7%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.WAITthe mixture is kept for 4 hours at room temperature
  2. 2
    Другоеthe precipitate obtained
  3. 3
    Фильтрацияis filtered off
  4. 4
    Промывкаwashed with water
  5. 5
    Экстракцияextracted with chloroform
  6. 6
    Промывкаthe extract is washed with water
  7. 7
    Другоеthe organic layer is dried
  8. 8
    Другоеthe solvent is evaporated off
  9. 9
    Другоеthe residue is recrystallized from an ethanol/water mixture (1:1)

Методика

A mixture of 1.5 g (0.005 mol) of ethyl 6-fluoro-7-(pyrrol-1-yl)-1-formylamino-4-oxo-1,4-dihydroquinoline-3-carboxylate and 1.3 g (0.01 mol) of potassium carbonate in 10 ml of dimethylformamide is stirred for 3 hours at room temperature, 2.35 g (0.015 mol) of ethyl iodide are then added and the mixture is kept for 4 hours at room temperature. It is poured into a water/ice mixture, the precipitate obtained is filtered off, washed with water and extracted with chloroform, the extract is washed with water, the organic layer is dried, the solvent is evaporated off and the residue is recrystallized from an ethanol/water mixture (1:1) to give 0.7 g of a solid melting at 192°-194° C.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US04727080uspto-grants-1988_02