Water → 1-Chloro-7-trifluoromethyl-2-aminonaphthalene

Reaktionsgleichung

[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH:16]C(=O)C.O.S(=O)(=O)(O)O>C(O)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([F:14])([F:15])[F:13])[CH:10]=2)[CH:5]=[CH:4][C:3]=1[NH2:16]

Komponenten

Versuchsvorschrift

A mixture of 1-chloro-7-trifluoromethyl-2-acetamidonaphthalene (700 mg, 2.43 mmol), water (3 mL) and concentrated sulfuric acid (3 mL in ethanol (6 mL) is heated to reflux temperature under a N2 atmosphere for 1 hour. After cooling to room temperature, the mixture is extracted with EtOAc. The extracts are washed with water, brine, dried (Na2SO4) and concentrated. Flash chromatography on silica gel (3:1 hexanes/EtOAc) gives 1-chloro-7-trifluoromethyl-2-aminonaphthalene as a white solid.