反应详情

To a stirred solution of methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate (156 mg, 0.63 mmol) in methanol (1.3 mL) was added potassium hydroxide (6.3 mL of a 1 M solution in water, 6.3 mmol). The reaction mixture was stirred at room temperature for 48 h and concentrated under reduced pressure. The residue was diluted with water and washed with ethyl acetate. The aqueous layer was acidified to pH 4 with 1 N hydrochloric acid and extracted with chloroform (4×100 mL). The combined organic extracts were dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 methanol/chloroform) afforded 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid (139 mg): ESI MS m/z 234 [M+H]+.

1. concentrationconcentrated under reduced pressure
2. additionThe residue was diluted with water
3. washwashed with ethyl acetate
4. extractionextracted with chloroform (4×100 mL)
5. dry with materialThe combined organic extracts were dried (sodium sulfate)
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customPurification by flash column chromatography (silica, 1:9 methanol/chloroform)