2-amino-3,4-dihydro-2H-naphthalen-1-one;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Chloroacetyl chloride (14 g, 124 mmol) was added to a solution of 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16 g, 81 mmol) and triethylamine (41 g, 405 mmol) in tetrahydrofuran (600 ml) and the mixture was stirred for one hour. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (7.58 g, 31.9 mmol, 39%) as white crystals. The solution was partitioned between water and ethyl acetate The organic layer was washed with brine dried over magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Chloroacetyl chloride (14 g, 124 mmol) was added to a solution of 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16 g, 81 mmol) and triethylamine (41 g, 405 mmol) in tetrahydrofuran (600 ml) and the mixture was stirred for one hour. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (7.58 g, 31.9 mmol, 39%) as white crystals. The solution was partitioned between water and ethyl acetate The organic layer was washed with brine dried over magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (16.5 g, 81 mmol) was added to 3N aqueous hydrochloric acid (270 ml) and stirred at 100° C. for 5 hours. After removal of the solvent, the precipitate was filtered, washed with ethanol, and dried to give 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16.0 g, 81 mmol, 100%) as white crystals. After removal of the solvent the precipitate was filtered washed with ethanol dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of sodium bicarbonate (4.0 g) in water (50 ml) layered with ethyl acetate (200 ml) was added solid 2-amino-3,4-dihydronaphthalen-1(2H)-one hydrochloride (4.0 g, 2 mmol). After the solid had dissolved chloroacetylchloride (1.6 ml, 2 mmol) was added dropwise over 10 minutes. After stirring for 1 hr, the ethyl acetate layer was separated, washed with brine and dried over Na2SO4. Evaporation afforded 2.7 g (57%) of a dark solid; m.p. 118°-122° C. The product was purified by chromatography on silica using ethyl acetate: hexane (1:1 v/v) to elute, m.p. 121°-123° C. was added dropwise over 10 minutes the ethyl acetate layer was separated washed with brine dried over Na2SO4 Evaporation

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Chloroacetyl chloride (14 g, 124 mmol) was added to a solution of 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16 g, 81 mmol) and triethylamine (41 g, 405 mmol) in tetrahydrofuran (600 ml) and the mixture was stirred for one hour. The solution was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (7.58 g, 31.9 mmol, 39%) as white crystals. The solution was partitioned between water and ethyl acetate The organic layer was washed with brine dried over magnesium sulfate concentrated under reduced pressure The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: N-(1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (16.5 g, 81 mmol) was added to 3N aqueous hydrochloric acid (270 ml) and stirred at 100° C. for 5 hours. After removal of the solvent, the precipitate was filtered, washed with ethanol, and dried to give 2-amino-3,4-dihydro-2H-naphthalen-1-one hydrochloride (16.0 g, 81 mmol, 100%) as white crystals. After removal of the solvent the precipitate was filtered washed with ethanol dried

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a stirred solution of sodium bicarbonate (4.0 g) in water (50 ml) layered with ethyl acetate (200 ml) was added solid 2-amino-3,4-dihydronaphthalen-1(2H)-one hydrochloride (4.0 g, 2 mmol). After the solid had dissolved chloroacetylchloride (1.6 ml, 2 mmol) was added dropwise over 10 minutes. After stirring for 1 hr, the ethyl acetate layer was separated, washed with brine and dried over Na2SO4. Evaporation afforded 2.7 g (57%) of a dark solid; m.p. 118°-122° C. The product was purified by chromatography on silica using ethyl acetate: hexane (1:1 v/v) to elute, m.p. 121°-123° C. was added dropwise over 10 minutes the ethyl acetate layer was separated washed with brine dried over Na2SO4 Evaporation