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Chemical Structure| 1184920-35-1 Chemical Structure| 1184920-35-1

Structure of 1184920-35-1

Chemical Structure| 1184920-35-1

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Product Details of [ 1184920-35-1 ]

CAS No. :1184920-35-1
Formula : C11H9NO3
M.W : 203.19
SMILES Code : O=C(C1=CC2=C(C(NC=C2)=O)C=C1)OC
English Name :Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate
MDL No. :MFCD12407885

Safety of [ 1184920-35-1 ]

Application In Synthesis of [ 1184920-35-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 1184920-35-1 ]

[ 1184920-35-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1184920-35-1 ]
  • [ 1301214-60-7 ]
YieldReaction ConditionsOperation in experiment
48% Stage #1: 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In water 4 1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid To a mixture of methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate (25 g, 0.133 mol), tetrahydrofuran (200 mL) and water (200 mL) was added lithium hydroxide (16.8 g, 0.40 mol) at room temperature, and the mixture was stirred for four hours. Thin layer chromatography (petroleum ether/ethyl acetate=1:1) indicated the reaction was complete. The reaction mixture was extracted with ethyl acetate (100 mL*3) to remove impurities. The aqueous layer was acidified with 4 N aqueous HCl to pH 5 and filtered. The solid was dried in vacuum to give 1-oxo-1,2-dihydroisoquinoline-6-carboxylic acid (11.3 g, 48%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.48 (s, 1H), 8.24 (d, 2H), 7.93 (d, 1H), 7.22 (d, 1H), 6.68 (d, 1H).
Stage #1: 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In water 4 To a mixture of methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate (25 g, 0.133 mol), tetrahydrofuran (200 mL) and water (200 mL) was added lithium hydroxide (16.8 g, 0.40 mol) at room temperature, and the mixture was stirred for four hours. Thin layer chromatography (petroleum ether/ethyl acetate = 1 :1 ) indicated the reaction was complete. The reaction mixture was extracted with ethyl acetate (100 mL x 3) to remove impurities. The aqueous layer was acidified with 4 N aqueous HCI to pH 5 and filtered. The solid was dried in vacuum to give 1 -oxo-1 , 2- dihydroisoquinoline-6-carboxylic acid (1 1 .3 g, 48%) as a light yellow solid. 1H NMR (400 MHz, DMSO-c/e) ppm 11.48 (s, 1 H), 8.24 (d, 2H), 7.93 (d, 1 H), 7.22 (d, 1 H), 6.68 (d, 1 H).
Stage #1: 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester With lithium hydroxide In dimethyl sulfoxide at 100℃; for 16h; Stage #2: With hydrogenchloride In water Acidic conditions; 22 Heat l-Oxo-l,2-dihydro-isoquinoline-6-carboxylic acid methyl ester (3.1 lg, 15.3 mmol) in a mixture of DMSO and 2 M lithium hydroxide (30 mL) at 100 °C for 16 hours. Treat the reaction mixture with 1M hydrochloric acid, and collect the resulting white precipitate by filtration, rinsing with water and MeOH . Dry under high vacuum in the presence of P2O5 to give 2.87 g of the title compound.
Stage #1: 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester With water; lithium hydroxide In tetrahydrofuran at 20℃; for 4h; Stage #2: With hydrogenchloride In water 30.1 A mixture of 6-bromoisoquinolin-1(2H)-one (30 g, 0.134 mol), triethylamine (17.6 g, 0.174 mol), palladium(II) chloride (0.24 g, 1.34 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.84 g, 1.34 mmol) in methanol (300 mL) was pressurized with 2 MPa of carbon monoxide. The reaction was heated to 100° C. and stirred for 12 hours. The reaction mixture was filtered through Celite and concentrated. The residue was washed with water and the solid was dried under vacuum to give crude methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate (23.8 g, 95.2%) as a yellow solid. The solid was diluted with tetrahydrofuran (200 mL) and water (200 mL). To this mixture was added lithium hydroxide (16.8 g, 0.4 mol) and the reaction was stirred at room temperature for 4 hours. The reaction mixture was washed with ethyl acetate (3×) and these washings were discarded. The aqueous layer was acidified with 4 N aqueous hydrochloric acid to pH=5. The resulting precipitate was collected by filtration and dried under vacuum to give the title compound (11.3 g, 49%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 11.48 (s, 1H), 8.24 (d, 2H), 7.93 (d, 1H), 7.22 (d, 1H), 6.68 (d, 1H).

 

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