3-methoxynaphthalen-2-amine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-amino-3-methoxynaphthalene (0.253 g, 1.50 mmol) in CH2Cl2 (3 mL) at room temp. was added a solution of 1-naphthyl isocyanate (0.247 g, 1.50 mmol) in CH2Cl2 (2 mL) and the resulting mixture was allowed to stir overnight. The resulting precipitate was separated and washed with CH2Cl2 to give the desired urea as a white powder (0.450 g, 90%): mp 235-236° C.; 1H-NMR (DMSO-d6) δ 4.04 (s, 3H), 7.28-7.32 (m, 2H), 7.38 (s, 1H), 7.44-7.72 (m, 6H), 7.90-7.93 (m, 1H), 8.05-8.08 (m, 1H), 8.21-8.24 (m, 1H), 8.64 (s, 1H), 9.03 (s, 1H), 9.44 (s, 1H); FAB-MS m/z 343 ((M+H)+). B1f. General Method for the Reaction of an Aryl Amine with an Aryl Isocyanate The resulting precipitate was separated washed with CH2Cl2

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3-Amino-2-naphthol (7.96 g, 50.0 mmol) was dissolved in N-methylpyrrolidone (190 ml), and the mixture was stirred under ice-cooling. Then, 60% sodium hydride (2.08 g, 52 mmol) was added, and the mixture was stirred at the same temperature for 40 min. Then, ethyl iodide (3.3 ml, 53 mmol) was added, and the mixture was stirred at the same temperature for 2 hr. To the reaction mixture was added diluted aqueous sodium hydroxide solution, and the mixture was extracted with an ethyl acetate-hexane=1:1 mixed solvent. The organic layer was washed with diluted aqueous sodium hydroxide solution, water and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane), and the obtained solid was washed with hexane and dried under reduced pressure to give the title compound (4.53 g, yield 52%) as a colorless solid. cooling the mixture was stirred at the same temperature for 40 min the mixture was stirred at the same temperature for 2 hr the mixture was extracted with an ethyl acetate-hexane=1:1 mixed solvent The organic layer was washed with diluted aqueous sodium hydroxide solution, water and saturated brine dried over anhydrous magnesium sulfate The insoluble material was filtered off the solution was concentrated under reduced pressure The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane) the obtained solid was washed with hexane dried under reduced pressure