1: 2-aminonaphthalene-3-carboxylic acid methyl ester With hydrogenchloride; sodium nitrite in water T=0°C; 1 h; 2: KSeCN With sodium acetate in water T=0 - 20°C;

1.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 1.2: 93 percent / hydrochloric acid; air / diethyl ether 2.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 View Scheme

1.1: lithium aluminum hydride / diethyl ether / 2 h / Heating 1.2: 93 percent / hydrochloric acid; air / diethyl ether 2.1: 76 percent / thionyl chloride; pyridine / CH2Cl2 3.1: 38 percent / potassium fluoride; calcium fluoride / various solvent(s) / 85 h / Heating View Scheme