Sulfuric Acid → 8-Azidonaphthalen-1-ol

Reaktionsgleichung

[N:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:13]=1[C:12](N)=[CH:11][CH:10]=[CH:9]2)=[N+:2]=[N-:3].S(=O)(=O)(O)[OH:16].N([O-])=O.[Na+]>O>[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][C:12]=2[OH:16])[CH:7]=[CH:6][CH:5]=1)=[N+:2]=[N-:3]

Komponenten

Versuchsvorschrift

A sample of 8-azido-1-naphthylamine (0.368 g., 0.02 mole) was dissolved in warm, dilute sulfuric acid (3 ml. of conc. H2SO4 diluted with 30 ml. of water). The solution was cooled to O°C. and diazotized with a solution of NaNO2 (160 mg., 0.023 mole) in 2 ml. of water. The excess of nitrous acid was destroyed by the addition of urea. The yellow solution of the diazonium salt was diluted with 100 ml. of water and heated at 60°for 1.5 hr. The precipitated material was washed with water, dried and filtered through activated charcoal. Removal of ether left a residue which weighed 35 mg. Recrystallization from petroleum ether gave 1-azido-8-hydroxynaphthalene in the form of pale yellow needles (20 mg., 5.4 percent), m.p. 65°C.-67°C.