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With 10 wt% Pd(OH)2 on carbon; hydrogen; acetic acid; In tetrahydrofuran; at 50℃; under 7757.43 Torr; for 16h;
1,4-Dimethoxy-2-nitro-3 - [(E) -2-nitroethenyl] benzene (6.56 g)In tetrahydrofuran (100 mL)Palladium hydroxide / carbon (2 g)And acetic acid (4.2 mL)Hydrogen was added at 150 psi and stirred at 50 C. for 16 h.After cooling the reaction solution to room temperature,The solution obtained by filtration was washed with a 5% sodium bicarbonate aqueous solution.The organic layer was dried over sodium sulfate,The solvent was evaporated under reduced pressure to obtain a residue,Purification by silica gel column chromatography (hexane-ethyl acetate),4,7-Dimethoxy-1H-indole2.9 g (yield 63%) was obtained.
General procedure: A cold solution of dimethoxyindole in DMF (1.5 mL) was added to a mixture of DMF (3.0 eq) and POCl3 (1.5 eq) at -20 C (ice-salt bath).The reaction mixture was stirred at-20 C for an additional 1 h to yield dimethoxyindole-3-carboxaldehyde. An aqueous solution of HONH2·HCl (1.2 eq) and NaOAc (1.2 eq) in H2O (1 mL) was added to dimethoxyindole-3-carboxaldehyde in EtOH (3.0 mL) and the reaction mixture was stirred at rt. After 2 h, EtOH was removed, the residue was diluted with H2O and was extracted with EtOAc to yield dimethoxyindole-3-carboxaldehyde oxime. Acetic anhydride (2.2 eq) was addedto a solution of dimethoxyindole-3-carboxaldehyde oxime in pyridine(1.5 mL) and the reaction mixture was heated at 75 C for different times, as mentioned below for each nitrile. Pyridine was removed in a rotary evaporator after dilution with toluene to afford dimethoxyindole-3-carbonitrile, as shown below for each compound.
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