4-amino-3-methoxyphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (60 wt %, 3.2 g) was added to dimethyl sulfoxide (50 ml), and the mixture was stirred at 50° C. for 20 min. 4-Amino-3-methoxyphenol (5.6 g) was added thereto, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinazoline (7.0 g) was added thereto, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. Methanol was added to the residue, and the precipitated crystal was collected by suction filtration to give the title compound (7.3 g, yield 72%). the mixture was stirred at room temperature for 10 min the mixture was stirred at 100° C. overnight the mixture was extracted with chloroform The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure Methanol was added to the residue the precipitated crystal was collected by suction filtration

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

Procedure: 4-Amino-3-methoxyphenol (5.88 g) was dissolved in dimethyl sulfoxide (80 ml) while stirring, and then 60% sodium hydride (1.6 g) was added thereto gradually under a nitrogen stream, followed by stirring for 20 min. 2-amino-4-chloropyridine (2.75 g) was then added thereto, followed by stirring at 160° C. for 8 hrs. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and water. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether was then added to precipitate crystals. The crystals were filtered and dried under aeration to provide the titled compound (1.56 g, 34%) as pale brown crystals. by stirring for 20 min by stirring at 160° C. for 8 hrs partitioned between ethyl acetate and water The organic layer was washed with water and brine in this order dried over anhydrous sodium sulfate The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent Fractions containing the target compound were concentrated to give a residue to precipitate crystals The crystals were filtered dried under aeration

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

Procedure: 1-Benzyloxy-3-methoxy-4-nitrobenzene (11.0 g) was dissolved in tetrahydrofuran (100 ml)-methanol (100 ml), and then 10% palladium carbon (5.0 g) was added thereto, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order. The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum to provide the titled compound (5.88 g, quantitatively) as brown powder. the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum

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

Procedure: 1-Benzyloxy-3-methoxy-4-nitrobenzene (11.0 g) was dissolved in tetrahydrofuran (100 ml)-methanol (100 ml), and then 10% palladium carbon (5.0 g) was added thereto, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order. The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum to provide the titled compound (5.88 g, quantitatively) as brown powder. the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 4-Amino-3-methoxyphenol (21 g) and ethyl 2-butyryl-3-ethoxyacrylate (36 g) were heated together at 90°-110° for 30 minutes to afford ethyl 2-butyryl-3-(4-hydroxy-2-methoxyphenylamino)acrylate (46.1 g, 77%) as a brown solid, m.p. 140°-142°.

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

Procedure: Sulphanilic acid (43.3 g) and anhydrous sodium carbonate (13.25 g) were dissolved in water (250 ml) and cooled to 15 C. Sodium nitrite (18.5 g) in water (100 ml) was added and the mixture was immediately poured onto a mixture of ice (300 ml) and hydrochloric acid (54 ml), and stirred at 0° for 20 minutes. The suspension was then added to a cooled solution of 3-methoxyphenol (31 g) and sodium hydroxide (55 g) in water (300 ml). The resulting deep red solution was stirred for 1 hour then heated to 70°. Sodium dithionite was added portionwise until the colour discharged on cooling, crystals of 4-amino-3-methoxyphenol (23 g, 66%) formed which were filtered, washed with water and dried, m.p. 168°-170°. cooled to 15 C The resulting deep red solution was stirred for 1 hour then heated to 70° on cooling

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium hydride (60 wt %, 3.2 g) was added to dimethyl sulfoxide (50 ml), and the mixture was stirred at 50° C. for 20 min. 4-Amino-3-methoxyphenol (5.6 g) was added thereto, and the mixture was stirred at room temperature for 10 min. Next, 4-chloro-6,7-dimethoxyquinazoline (7.0 g) was added thereto, and the mixture was stirred at 100° C. overnight. Water was added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. Methanol was added to the residue, and the precipitated crystal was collected by suction filtration to give the title compound (7.3 g, yield 72%). the mixture was stirred at room temperature for 10 min the mixture was stirred at 100° C. overnight the mixture was extracted with chloroform The chloroform layer was then washed with a saturated aqueous sodium hydrogencarbonate solution was dried over anhydrous sodium sulfate The solvent was removed by distillation under the reduced pressure Methanol was added to the residue the precipitated crystal was collected by suction filtration

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

Procedure: 4-Amino-3-methoxyphenol (5.88 g) was dissolved in dimethyl sulfoxide (80 ml) while stirring, and then 60% sodium hydride (1.6 g) was added thereto gradually under a nitrogen stream, followed by stirring for 20 min. 2-amino-4-chloropyridine (2.75 g) was then added thereto, followed by stirring at 160° C. for 8 hrs. The reaction mixture was cooled down to room temperature, and partitioned between ethyl acetate and water. The organic layer was washed with water and brine in this order, and dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent; ethyl acetate, then ethyl acetate:methanol=9:1). Fractions containing the target compound were concentrated to give a residue, to which diethyl ether was then added to precipitate crystals. The crystals were filtered and dried under aeration to provide the titled compound (1.56 g, 34%) as pale brown crystals. by stirring for 20 min by stirring at 160° C. for 8 hrs partitioned between ethyl acetate and water The organic layer was washed with water and brine in this order dried over anhydrous sodium sulfate The solvent was evaporated under a reduced pressure to give a residue, which was then purified by silica gel column chromatography (eluent Fractions containing the target compound were concentrated to give a residue to precipitate crystals The crystals were filtered dried under aeration

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

Procedure: 1-Benzyloxy-3-methoxy-4-nitrobenzene (11.0 g) was dissolved in tetrahydrofuran (100 ml)-methanol (100 ml), and then 10% palladium carbon (5.0 g) was added thereto, followed by replacing with hydrogen inside the system and stirring overnight. After replacing with nitrogen inside the system, the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order. The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum to provide the titled compound (5.88 g, quantitatively) as brown powder. the reaction mixture was filtered to remove the catalyst, which was washed with tetrahydrofuran, ethyl acetate and methanol in this order The filtrate was concentrated under a reduced pressure to give a residue, which was dried in vacuum

Conditions: temp:0.00; pressure:0.00; stir: