Reaktion #40686

Reaktionsgleichung

8-amino-2-naphthol

phenyl chloroformate

sodium hydrogen carbonate

water

→

title compound

phenyl 7-hydroxy-1-naphthylcarbamate

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenAfter washing with 1N hydrochloric acid
2. 2
   Trocknenthe organic layer was dried over anhydrous sodium sulfate
3. 3
   Sonstigethe solvent was evaporated
4. 4
   workup.ADDITIONDiethyl ether and hexane were added to the residue
5. 5
   Filtrationthe precipitate was collected by filtration

Vorschrift

To 8-amino-2-naphthol (100 mg) were added phenyl chloroformate (87 μl), saturated aqueous sodium hydrogen carbonate (0.5 ml), dichloromethane (1 ml) and water (0.5 ml), and the mixture was stirred for 3 hrs. The reaction mixture was diluted with dichloromethane. After washing with 1N hydrochloric acid, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. Diethyl ether and hexane were added to the residue, and the precipitate was collected by filtration to give the title compound (160 mg). NMR data of Example 109: 1H-NMR (300 MHz, DMSO-d6) δ3.49 (2H, m), 4.06 (2H, s), 6.79 (4H, m), 7.10 (2H, m), 7.30 (2H, m), 7.75 (2H, m), 8.34 (1H, s), 9.69 (1H, s).

Quelle