Reaktionsgleichung
[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[OH-].[K+]>CO.O>[CH2:1]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=2)[CH2:8][CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]Komponenten
Versuchsvorschrift
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]+.
Aufarbeitung
- concentrationconcentrated under reduced pressure
- additionThe residue was diluted with water
- washwashed with ethyl acetate
- extractionextracted with chloroform (4×100 mL)
- dry with materialThe combined organic extracts were dried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customPurification by flash column chromatography (silica, 1:9 methanol/chloroform)
Quellen und Nachweise
- ORD-Eintrag
- ord-47a1a3aedd774fc1a74f03771b792dea
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07176242B2
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