| 91% |
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 20℃; |
22.2 Step (2) 4-methoxy-N1-methylbenzene-1,2-diamine
Compound 22-2 (3.8g, 20.87mmol) was dissolved in a mixed solution of ethanol (75mL) and tetrahydrofuran (15mL), a palladium/carbon catalyst (10%, 500mg) was added to it, and hydrogen was bubbled in and stirred at room temperature overnight . Filter out palladium on carbon,The filtrate was spin-dried. The crude product was purified by silica gel column (dichloromethane: ethyl acetate = 10:1) to obtain compound 22-3,Yellow solid (2.9 g, 91% yield). |
| 80% |
With hydrogenchloride; tin(ll) chloride at 25℃; for 1h; |
|
| 69% |
With palladium on activated charcoal; hydrogen In tetrahydrofuran; ethanol at 20℃; for 4h; |
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With hydrogenchloride; tin |
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With hydrogen In ethanol |
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With hydrogen In methanol |
|
| 1.5 g |
With hydrogen In methanol |
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In ethanol; palladium |
25 4-Methoxy-N-methyl-1,2-phenylenediamine
Preparation 25 4-Methoxy-N-methyl-1,2-phenylenediamine A solution of 1.16 g of N-methyl-4-methoxy-2-nitroaniline (prepared as described in Preparation 24) in 50 ml of ethanol was shaken in an atmosphere of hydrogen and in the presence of 0.3 g of 10% w/w palladium-on-charcoal for 3 hours. At the end of this time, the palladium-on-charcoal was filtered off, and the filtrate was freed from the solvent by evaporation under reduced pressure, to give 1.17 g of the title compound having an Rf value=0.50 (on thin layer chromatography on silica gel; developing solvent: a 1:3 by volume mixture of ethyl acetate and hexane). |
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In ethanol; palladium |
25 4-Methoxy-N-methyl-1,2-phenylenediamine
PREPARATION 25 4-Methoxy-N-methyl-1,2-phenylenediamine A solution of 1.16 g of N -methyl-4-methoxy-2-nitroaniline (prepared as described in Preparation 24) in 50 ml of ethanol was shaken in an atmosphere of hydrogen and in the presence of 0.3 g of 10% w/w palladium-on-charcoal for 3 hours. At the end of this time, the palladium-on-charcoal was filtered off, and the filtrate was freed from the solvent by evaporation under reduced pressure, to give 1.17 g of the title compound having an Rf value = 0.50 (on thin layer chromatography on silica gel; developing solvent: a 1: 3 by volume mixture of ethyl acetate and hexane). |
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With hydrogenchloride; tin In ethanol for 0.5h; Heating; |
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With hydrogen In ethyl acetate for 3h; |
25
4-Methoxy-2-nitrophenylamine (5.0 g, 30 mmol) was dissolved in DMF (50 mL) and cooled to 10 C. NaH (63% in oil, 1.3 g, 33 mmol) was added portionwise and the mixture stirred for 30 min. Methyl iodide (2.1 mL, 33 mmol) was added and after 30 min the mixture was quenched with water. The resulting solid was collected by filtration and diluted with ethyl acetate (200 mL). 5% Pd/C (1.0 g) was added and the mixture was shaken under an atmosphere of hydrogen at 50 psi for 3 h. The reaction mixture was filtered through a pad of Celite and concentrated to give 4-Methoxy-N1-methyl-benzene-1,2-diamine (1.0 g). This material was heated in formic acid (2 mL) at 100 C for 90 min. The mixture was cooled to rt, diluted with EtOAc and quenched with sat. NaHCO3 until basic. The organic phase was collected, dried and concentrated to give 5-methoxy-1-methyl-1H-benzoimidazole (0.9 g) which was converted to the title compounds using the method described in Preparation 23. |
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With hydrogen In ethyl acetate at 20℃; for 6h; |
378.B
Step B. 4-methoxy-N 1 -methyl-benzene- 1 ,2-diamine:A stirred solution of 4-methoxy-2-nitro-phenyl)-methyl-amine (2.5 g5 0.013mol) in ethyl acetate (25 ml) was hydrogenated using 10% Pd/C for 6h at room temperature. The reaction was filtered through CELITE and the bed was thoroughly washed with EtOAc. The resulting solution was concentrated to provide 4~methoxy-Nl -methyl-benzene- 1,2-diamine as a brown solid. C8H12N20; Crude 1H NMR (400 MHz, DMSO-rfi), δ: 6.27 (d, J= 8.8 Hz, 1H), 6.19 (d, J- 2.8 Hz, 1H), 6.07 (dd, Ji = 8.4 Hz, J2 = 2.4 Hz, 1H), 4.49 (s, 2H), 4.08 (s, 1H), 3.56 (s, 3H)} 2.63 (s, 3H). MS (M+l): 153.2. |
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With sodium dithionite In tetrahydrofuran; ethanol; water at 0 - 20℃; for 4h; |
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With hydrogenchloride; iron In ethanol; water at 95℃; Inert atmosphere; |
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