104447-80-5|Methyl (E)-4-(2-(dimethylamino)vinyl)-3-nitrobenzoate|Ambeed

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CAS No. :	104447-80-5
Formula :	C₁₂H₁₄N₂O₄
M.W :	250.25
SMILES Code :	CN(C)/C=C/C1=C(C=C(C(OC)=O)C=C1)N(=O)=O
MDL No. :	MFCD03924986

Yield	Reaction Conditions	Operation in experiment
85%	In tetrahydrofuran; palladium; ethyl acetate;	b. Methyl indole-6-carboxylate A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydrofuran (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 min. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine; then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3): 3.92(s, 3H, OCH3), 6.57(m, 1H, H3 -indole), 7.32(t, 1H, H2 -indole), 7.10(d, 1H, H4 -indole), 7.87(dd, 1H, H5 -indole), 8.16(broad s, 1H, H7 -indole).
85%	In tetrahydrofuran; palladium; ethyl acetate;	(b) A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydrofuran (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 minutes. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine, then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3) 3.92(s, 3H, OCH3), 6.57(m, 1H, H3 -indole), 7.32(t, 1H, H2 -indole), 7.10(d, 1H, H4 -indole), 7.87(dd, 1H, H5 -indole), 8.16(broad s, 1H, H7 -indole).
85%	In tetrahydrofuran; palladium; ethyl acetate;	(b) A solution of methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (5.58 g) in tetrahydro-furan (100 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium on carbon (1.1 g) for 35 minutes. The catalyst was removed by filtration through diatomaceous earth and the filtrate was evaporated. The residue was dissolved in ethyl acetate and the solution obtained was washed successively with 10% (v/v) hydrochloric acid, water, and brine, then dried (MgSO4) and evaporated to give methyl indole-6-carboxylate (3.32 g, 85%) as a white solid; NMR (80 MHz, CDCl3): 3.92(s, 3H, OCH3), 6.57(m, 1H, H3-indole), 7.32(t, 1H, H2-indole), 7.10(d, 1H, H4-indole), 7.87(dd, 1H, H5-indole), 8.16(broad s, 1H, H7-indole).

84%	With hydrogen;palladium on activated charcoal; In tetrahydrofuran; at 20℃;	Step 3. Methyl 1H-indole-6-carboxylate A solution of (E)-methyl 4-(2-(dimethylamino)vinyl)-3-nitrobenzoate (2.2 g, 8.80 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) was placed into a 100-mL round-bottom flask. Then 2.4 g of palladium on carbon was added. An atmosphere of hydrogen gas was placed over the contents of the flask, and the reaction was stirred overnight at room temperature. Then the solids were filtered off, and the resulting mixture was concentrated in vacuo. This resulted in 1.3 g (84%) of methyl 1H-indole-6-carboxylate as brown oil.
	With sodium dithionite; In tetrahydrofuran; ethanol; water;	Production Example 5 6-methoxycarbonylindole To a mixed solvent of tetrahydrofuran (30 ml), ethanol (30 ml) and water (100 ml), added are methyl E-4-(2-dimethylaminovinyl)-3-nitrobenzoate (10.0 g) and sodium hydrosulfite (104.5 g), and stirred at 70 C. for 1 hours. After this is cooled to room temperature, a saturated saline solution is added thereto. Then, this is extracted with chloroform. The organic layer is dried, and the solvent is evaporated away. The resulting residue is purified through silica gel column chromatography (eluent: hexane/ethyl acetate=2/1 to 1/1) to obtain 6-methoxycarbonylindole (2.79 g). 1H-NMR (CDCl3, δ): 3.93 (3H, s), 6.60 (1H, s), 7.37 (1H, m), 7.66 (1H, d, J=8.3 Hz), 7.81 (1H, dd, J=1.3 and 8.3 Hz), 8.17 (1H, s), 8.52 (1H, brs).
	palladium-carbon; In tetrahydrofuran;	EXAMPLE 1 Methyl 6-indolecarboxylate STR8 16.7 g (0.060 mol) of methyl 4-(2-dimethylaminoethenyl)-3-nitrobenzoate [prepared according to the general working procedure of L. F. Tietze and Th. Eicher, "Reaktionen und Synthesen" (Reactions and Syntheses), p. 172, Thieme, Stuttgart 1981] were hydrogenated in 300 ml of tetrahydrofuran containing 1.1 g of palladium carbon (10%). The solution was filtered for 2 hours through kieselguhr and the catalyst was washed with 50 ml of tetrahydrofuran. The solvent was removed in vacuo. In order to remove a small amount of impurity (methyl 3-amino-4-methylbenzoate), the product was washed successively with 10% strength hydrochloric acid, water and concentrated sodium chloride solution, dried over magnesium sulphate and concentrated on a rotary evaporator. Yield: 9.9 g (94% of theory) of yellow crystals Rf (CH2 Cl2)=0.38 Rf (CH2 Cl2, 5% MeOH)=0.53

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CAS No.: 104447-80-5

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CAS No.: 104447-80-5

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