methyl 2-oxo-3,4-dihydro-1H-quinoline-3-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 1N Aqueous sodium hydroxide solution (80 ml) was added dropwise to the mixed solution of methyl 2-oxo-1,2,3,4-tetrahydro-3-quinolinecarboxylate (8.322 g) in THF (80 ml) and methanol (80 ml) at 0° C. The reaction mixture was stirred at room temperature for 4 hours. 1N Hydrochloric acid (90 ml) was added dropwise to the reaction mixture at 0° C., which was then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated to obtain crude crystals of the entitled compound (7.032 g). The obtained crude crystals were put to use in the following reaction without purification. which was then extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium chloride solution dried concentrated

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium borohydride (1.10 g) was added to the mixed solution of dimethyl 2-[(2-nitrophenyl)methylidene]malonate (15.2 g) in ethyl acetate (50 ml) and methanol (200 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes. Water was added to the mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) and methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days. The catalyst was removed by filtration, and the filtrate was concentrated. The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4 to give the entitled compound (9.487 g). was extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium chloride solution dried concentrated 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days The catalyst was removed by filtration the filtrate was concentrated The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium borohydride (1.10 g) was added to the mixed solution of dimethyl 2-[(2-nitrophenyl)methylidene]malonate (15.2 g) in ethyl acetate (50 ml) and methanol (200 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes. Water was added to the mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) and methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days. The catalyst was removed by filtration, and the filtrate was concentrated. The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4 to give the entitled compound (9.487 g). was extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium chloride solution dried concentrated 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days The catalyst was removed by filtration the filtrate was concentrated The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Sodium borohydride (1.10 g) was added to the mixed solution of dimethyl 2-[(2-nitrophenyl)methylidene]malonate (15.2 g) in ethyl acetate (50 ml) and methanol (200 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes. Water was added to the mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) and methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days. The catalyst was removed by filtration, and the filtrate was concentrated. The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4 to give the entitled compound (9.487 g). was extracted with ethyl acetate The organic layer was washed with a saturated aqueous sodium chloride solution dried concentrated 5% Palladium-carbon (6.26 g) was added to the mixed solution of the residue in THF (100 ml) methanol (100 ml), and catalytic hydrogenation was conducted at room temperature under atmospheric pressure for 3 days The catalyst was removed by filtration the filtrate was concentrated The obtained crude crystals were washed with a mixed solution of ethyl acetate/hexane=1/4