* 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.
With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;
2-Chloro-3-nitroanisole C3 (1.38 g; 7.36 MMOL) was dissolved in a mixture of glacial acetic acid (19 ML)/ETHANOI (19 mL). To this solution was added iron powder (1.64 g; 29.4 MMOL). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid NA2CO3 and the product extracted with CH2CI2 (3X 150 mL). The extracts were combined and washed with saturated. brine and then dried(NA2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline C4 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps. MS 157.9 (MH) + ; Homogeneity by HPLC (TFA) 220 nm: 86%.
100%
With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;
Step C:; 2-Chloro-3-nitroanisole 1c2 (1.38 g; 7.36 mmol) was dissolved in a mixture ofglacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder(1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. Thereaction mixture was diluted with water (70 ml_), neutralized with solid Na2CO3 and theproduct extracted with CH2CI2 (3 X 150 ml). The extracts were combined and washedwith sat. brine and then dried(Na2SO4), filtered and concentrated in vacua toafford the crude product, 2-chloro-3-methoxyaniline 1c3 (100%; 1.2 g) as a yellow oil.This material was used as such in the following steps. MS 157.9 (MH)+; Homogeneityby HPLC (TFA) (at) 220nm: 86%.
100%
With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;
2-Chloro-3-nitroanisole 1c2 (1.38 g; 7.36 mmol) was dissolved in a mixture of glacial acetic acid (19 mL)/ethanol (19 mL). To this solution was added iron powder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and worked up. The reaction mixture was diluted with water (70 mL), neutralized with solid Na2CO3 and the product extracted with CH2Cl2 (3*150 mL). The extracts were combined and washed with sat. brine and then dried(Na2SO4), filtered and concentrated in vacuo to afford the crude product, 2-chloro-3-methoxyaniline 1c3 (100%; 1.2 g) as a yellow oil. This material was used as such in the following steps. MS 157.9 (MH)+; Homogeneity by HPLC (TFA)a220 nm: 86%.
100%
With iron; acetic acid; In ethanol; for 3.5h;Heating / reflux;
2-Chloro-3-nitroanisole 2c2 (1.38 g; 7.36 mmol) was dissolved in a mixtureof glacial acetic acid (19 ml_ )/ethanol (19 ml_). To this solution was added ironpowder (1.64 g; 29.4 mmol). The mixture was stirred at reflux for 3.5 hr and workedup. The reaction mixture was diluted with water (70 ml), neutralized with solidNa2CO3 and the product extracted with CH2CI2( 3X 150 ml). The extracts werecombined and washed with sat. brine and then dried(Na2SO4), filtered andconcentrated in vacua to afford the crude product, 2-chloro-3-methoxyaniline 2c3(100%; 1.2 g) as a yellow oil. This material was used as such in the following steps.MS 157.9 (MH)+; Homogeneity by HPLC (TFA) (at) 220nm: 86%.
With iron; acetic acid; at 45 - 80℃; for 2h;
(iii) Iron powder (3.63 g, 65.0 mmol) was suspended in acetic acid (50 ml) and warmed to 4O0C with mechanical stirring. 2-Chloro-3-nitrophenyl methyl ether (2.44 g, 13.01 mmol) dissolved in acetic acid (25 ml) was added at such a rate as to maintain a temperature of 45-5O0C. The mixture was heated at 80 0C for 2 hours after the addition had been completed. The mixture was filtered through celite and concentrated in vacuo. The residue was partitioned between ethyl acetate and 10% 0.880 ammonia solution. Solids were removed by filtration through celite and the aqueous extracted in to ethyl acetate (x3). The combined extracts were washed with water, brine, dried over anhydrous sodium sulfate and concentrated to an oil. The crude product was purified by flash-silica gel chromatography, eluting with a 0-100% gradient of ethyl acetate in isohexane to afford 2-chloro-3-(methyloxy)aniline (1.66 g).
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