Sodium Hydroxide → 5-Cyclopropylamino-6-cyclopropylmethoxy-pyridine-2-carboxylic acid
Reaktionsgleichung
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:14][CH2:13]2)=[C:7]([O:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)[N:6]=1)=[O:4].[OH-].[Na+]>CO.C(OCC)(=O)C>[CH:12]1([NH:11][C:8]2[CH:9]=[CH:10][C:5]([C:3]([OH:4])=[O:2])=[N:6][C:7]=2[O:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)[CH2:13][CH2:14]1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
A solution of 5-(cyclopropylamino)-6-(cyclopropylmethoxy)-pyridine-2-carboxylic acid methyl ester (400 mg, 1.53 mmol), sodium hydroxide (244 mg, 6.1 mmol) in THF/H2O 1/1 (10 mL) was stirred for 1 h at room temperature. The reaction mixture was concentrated under reduced pressure. Water was added and the pH was adjusted to 2 by addition of 1 N HCl. Extraction with ethyl acetate (30 mL) was followed by washing with brine (6×30 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (silica gel, 50 g, 50% ethyl acetate in petroleum ether) to yield the title compound (350 mg, 92%) as yellow solid; MS (EI): m/e=249.3 [M+H]+.