Hydrogen Bromide → 6-Amino-2-naphthalenol

Participants

Reaction Steps

(6-Methoxy-naphthalen-2-yl)-carbamic acid tert-butyl ester (10.05 g, 36.8 mmol), prepared in the previous step, was suspended in 300 mL of glacial acetic acid plus 200 mL of 48% HBr and under nitrogen the mixture was refluxed for 6 h. The glacial acetic acid and the 48% HBr were removed under reduced pressure and the residue partitioned between methylene chloride and water. The aqueous layer was made basic by the addition of NaHCO3. A solid precipitated. The solid was collected by filtration and dried under reduced pressure to give 6-amino-naphthalen-2-ol (5.72 g, 98%) as a gray solid, MS m/z: 160 [M+H]+.

Provenance & Evidence