3-氨基-2-萘酚

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The urea was prepared from 3-amino 2-hydroxy napthalene (0.320 g, 2 mmol) and 2-bromo phenyl isocyanate (0.40 g) by general Method B. It was purified by dilution of the with methylene chloride and precipitation with hexane (0.339, 47%). EI-MS m/z 357 (M+H)+ It was purified by dilution of the with methylene chloride and precipitation with hexane (0.339, 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 3',5'-diacetyl-5bromo-2'-deoxyuridine (4.0 g; 10 mmol), methylene chloride (50 ml), triethylamine (4.0 g; 40 mmol) and DMAP (0.1 g) was added 2-mesitylsulfonyl chloride (4.4 g; 20 mmol). After stirring at room temperature for 6 h. DBU (3.0 g; 20 mmol) and 3-amino-2-naphthol (6.4 g; 40 mmol) were added and the solution was stirred for 4 h. at room temperature. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate aq. solution, but the title compound was precipitated from solution. The precipitates were filtered off and washed thoroughly with ethyl acetate, then methylene chloride, and dried. A small quantity of title compound also was obtained from the filtrate. the solution was stirred for 4 h. at room temperature The reaction mixture was concentrated the residue was dissolved in ethyl acetate washed with saturated sodium bicarbonate aq. solution the title compound was precipitated from solution The precipitates were filtered off washed thoroughly with ethyl acetate methylene chloride, and dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared by the method of Example 1a), from 3-amino-2-naphthol (476 mg, 2.9 mmol) and 4-methoxy-3-aminobenzoic acid (500 mg, 2.9 mmol) the subtitle compound was obtained, 120 mg (14%). 1H NMR (CDCl3) δ 8.06(s, 1H), 7.92–7.83(m, 3H), 7.67(dd, J=1.9, 8.2 Hz, 1H), 7.60(d, J=1.9 Hz, 1H), 7.38(m, 2H), 6.85(d, J=8.3 Hz, 1H), 3.88(s, 3H). MS 291 m/z (M+H)+.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared by the method of Example 1a), from 3-amino-2-naphthol (476 mg, 2.9 mmol) and 4-methoxy-3-aminobenzoic acid (500 mg, 2.9 mmol) the subtitle compound was obtained, 120 mg (14%). 1H NMR (CDCl3) δ 8.06(s, 1H), 7.92–7.83(m, 3H), 7.67(dd, J=1.9, 8.2 Hz, 1H), 7.60(d, J=1.9 Hz, 1H), 7.38(m, 2H), 6.85(d, J=8.3 Hz, 1H), 3.88(s, 3H). MS 291 m/z (M+H)+.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Prepared by the method of Example 1a), from 3-amino-2-naphthol (579 mg, 3.6 mmol) and 3-aminobenzoic acid (500 mg, 3.6 mmol) the subtitle compound was obtained, 58 mg (6%). 1H NMR (CDCl3) δ 8.12(s, 1H), 7.90(m, 3H), 7.65(dt, J=1.5, 7.5 Hz, 1H), 7.60(t, J=2.3 Hz, 1H), 7.42(m, 2H), 7.27(t, J=7.9 Hz), 6.82(dd, J=2.3, 7.9 Hz). MS 261 m/z (M+H)+.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 304 mg (1.91 mmol) of 3-amino-2-naphthol, 477 mg (1.81 mmol) of methyl 2-chloro-3,5-dinitrobenzoate and 178 mg (2.17 mmol) of sodium acetate were suspended in a mixture of water (5 ml) with ethanol (10 ml) and heated under reflux for 7 hours. After adding 3 ml of a 2 N aqueous solution of sodium hydroxide thereto, the reaction mixture was heated under reflux for additional 2.5 hours and then brought back to room temperature. After adding 10 ml of 1 N hydrochloric acid thereto, the precipitate thus formed was recovered by filtration and washed successively with water, 1 N hydrochloric acid and ethanol to thereby give 430 mg of 3-nitro-12H-benzo[b]phenoxazine-1-carboxylic acid. Then this product was treated by the same methods as those of Production Example 23 and Example 13 to thereby give the title compound. heated under reflux for 7 hours the reaction mixture was heated under reflux for additional 2.5 hours brought back to room temperature the precipitate thus formed was recovered by filtration washed successively with water, 1 N hydrochloric acid and ethanol

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 3',5'-diacetyl-5-bromo-2'-deoxyuridine (4.0 g; 10 mmol), methylene chloride (50 ml), triethylamine (4.0 g; 40 mmol) and DMAP (0.1 g) was added 2-mesitylsulfonyl chloride (4.4 g; 20 mmol). After stirring at room temperature for 6 h. DBU (3.0 g; 20 mmol) and 3-amino-2-naphthol (6.4 g; 40 mmol) were added and the solution was stirred for 4 h. at room temperature. The reaction mixture was concentrated, the residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate aq. solution, but the title compound was precipitated from solution. The precipitates were filtered off and washed thoroughly with ethyl acetate, then methylene chloride, and dried. A small quantity of title compound also was obtained from the filtrate. the solution was stirred for 4 h. at room temperature The reaction mixture was concentrated the residue was dissolved in ethyl acetate washed with saturated sodium bicarbonate aq. solution the title compound was precipitated from solution The precipitates were filtered off washed thoroughly with ethyl acetate methylene chloride, and dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The urea was prepared from 3-amino 2-hydroxy napthalene(0.320 g, 2 mmol) and 2-bromophenylisocyanate(0.40 g) by general Method B. It was purified by dilution of the with methylene chloride and precipitation with hexane(0.339, 47%). EI-MS m/z 357(M+H)+. It was purified by dilution of the with methylene chloride and precipitation with hexane(0.339, 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The urea was prepared from 3-amino 2-hydroxy napthalene(0.320 g, 2 mmol) and 2-bromophenylisocyanate(0.40 g) by general Method B. It was purified by dilution of the with methylene chloride and precipitation with hexane(0.339, 47%). EI-MS m/z 357(M+H)+. It was purified by dilution of the with methylene chloride and precipitation with hexane(0.339, 47%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Aminonaphthalen-2-ol (5 g, 31.4 mmol) is brought to the reflux point of 1-butanol (100 ml) in the presence of 2-chloro-N-(chloroethyl)-N-methylethanamine hydrochloride (6.05 g, 31.4 mmol) and sodium carbonate (1.7 g, 16 mmol). After 48 h, the reaction mixture is concentrated and impregnated onto silica and then purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia. the reaction mixture is concentrated purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 3-Aminonaphthalen-2-ol (5 g, 31.4 mmol) is brought to the reflux point of 1-butanol (100 ml) in the presence of 2-chloro-N-(chloroethyl)-N-methylethanamine hydrochloride (6.05 g, 31.4 mmol) and sodium carbonate (1.7 g, 16 mmol). After 48 h, the reaction mixture is concentrated and impregnated onto silica and then purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia. the reaction mixture is concentrated purified by flash chromatography with a mixture (93/7/1) of dichloromethane/methanol/aqueous ammonia

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The urea was prepared from 3-amino 2-hydroxy napthalene (0.320 g, 2 mmol) and 2-bromo phenyl isocyanate (0.40 g) by general Method B. It was purified by dilution of the with methylene chloride and precipitation with hexane (0.339, 47%). EI-MS m/z 357 (M+H)+ It was purified by dilution of the with methylene chloride and precipitation with hexane (0.339, 47%)