Reaktion #436215

Reaktionsgleichung

methyl 1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylate

potassium hydroxide

→

1-butyl-1,2,3,4-tetrahydroquinoline-7-carboxylic acid

Ausbeute 94.6%

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under reduced pressure
2. 2
   workup.ADDITIONThe residue was diluted with water
3. 3
   Waschenwashed with ethyl acetate
4. 4
   Extraktionextracted with chloroform (4×100 mL)
5. 5
   TrocknenThe combined organic extracts were dried (sodium sulfate)
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigePurification by flash column chromatography (silica, 1:9 methanol/chloroform)

Vorschrift

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]+.

Quelle