Реакция #91828

Уравнение реакции

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid

quinoline

→

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline

Выход 72.0%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураThe mixture was cooled
2. 2
   Фильтрацияfiltered over hyflo
3. 3
   ПромывкаThe filtrate was washed with 2 M hydrochloric acid (2×600 ml) and twice with 2 M sodium hydroxide (150 ml)
4. 4
   Другоеbefore being evaporated to dryness
5. 5
   ДругоеThe residue was purified by silica gel chromatography
6. 6
   Промывкаeluting with a ethyl acetate/hexanes (1:6)

Методика

5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylic acid (37.5 g, 0.186 mol), copper chromite (13.5 g, 43 mmol) and quinoline (180 ml) were heated with stirring to 185° C. for 2 hours. The mixture was cooled, diluted with dichloromethane (1 L) and filtered over hyflo. The filtrate was washed with 2 M hydrochloric acid (2×600 ml) and twice with 2 M sodium hydroxide (150 ml) before being evaporated to dryness. The residue was purified by silica gel chromatography, eluting with a ethyl acetate/hexanes (1:6) to afford 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (21 g, 72%) as a pale yellow solid. 1H NMR (CDCl3) 400 MHz δ: 7.44 (dd, 1H, J=0.8 and 7.6 Hz), 7.07 (d, 1H, J=3.2 Hz), 7.01 (t, 1H, J=7.2 Hz), 6.9 (dd, 1H, J=0.8 and 6.8 Hz), 6.43 (d, 1H, J=3.2 Hz), 4.16 (t, 2H, J=6 Hz), 2.99 (t, 2H, J=6.4 Hz), 2.24 (m, 2H).

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