反应详情

温度

90 °C

To a mixture of quinoline-5-carboxylic acid (4 g) in acetic acid (40 ml) was added borane-pyridine complex (8.59 g) at ambient temperature. After stirred for 18 hours, to the reaction mixture was added 1N hydrochloric acid and heated at 90° C. for 1 hour. The mixture was neutralized with aqueous sodium bicarbonate solution and ethyl acetate was added thereto. The precipitate was filtered off. The organic layer was separated, washed with water, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash silica gel chromatography eluted with chloroform-methanol and crystallized from diisopropyl ether to give 1,2,3,4-tetrahydroquinoline-5-carboxylic acid (1.12 g) as pale brown crystals.

1. additionwas added borane-pyridine complex (8.59 g) at ambient temperature
2. additionwas added
3. filtrationThe precipitate was filtered off
4. customThe organic layer was separated
5. washwashed with water
6. dry with materialdried over magnesium sulfate
7. customevaporated in vacuo
8. customThe residue was purified by flash silica gel chromatography
9. washeluted with chloroform-methanol
10. customcrystallized from diisopropyl ether