2-methoxybenzene-1,3-diamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.500 g (2.52 mmol) of compound 2,6-dinitroanisole was suspended in 40 mL of water together with 2.310 g (35.3 mmol) of Zn and 0.530 g (10.1 mmol) of NH4Cl. The solution was boiled for 2.5 h. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4 and distilled in vacuo to obtain 0.330 g (95%) of clean 2,6-diaminoanisole as a red oil. 1H NMR (CDCl3) δ 6.73 (t, J=7.9 Hz, 1H, Ar—H), 6.19 (d, J=7.9 Hz, 2H, Ar—H), 3.78 (s, 3H, O—CH3), 3.73 (br. s, 4H, Ar—NH2). 13C NMR (CDCl3) δ 140.3, 134.9, 125.2, 106.6, 58.6. the solution was extracted with ethyl acetate The organic solution was dried with anhydrous Na2SO4 distilled in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.500 g (2.52 mmol) of compound 2,6-dinitroanisole was suspended in 40 mL of water together with 2.310 g (35.3 mmol) of Zn and 0.530 g (10.1 mmol) of NH4Cl. The solution was boiled for 2.5 h. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4 and distilled in vacuo to obtain 0.330 g (95%) of clean 2,6-diaminoanisole as a red oil. 1H NMR (CDCl3) δ 6.73 (t, J=7.9 Hz, 1H, Ar—H), 6.19 (d, J=7.9 Hz, 2H, Ar—H), 3.78 (s, 3H, O—CH3), 3.73 (br. s, 4H, Ar—NH2). 13C NMR (CDCl3) δ 140.3, 134.9, 125.2, 106.6, 58.6. the solution was extracted with ethyl acetate The organic solution was dried with anhydrous Na2SO4 distilled in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-methoxy-1,3-dinitro-benzene (1.49 g) and palladium on carbon (10%, 150 mg) in ethanol (75 mL) was stirred under hydrogen atmosphere (1 atm.) overnight. The catalyst was filtered off on a CELITE™ pad and the filter cake was washed with ethanol. The filtrate was evaporated under reduced pressure to afford 1.1 g of 2-methoxy-benzene-1,3-diamine as a light yellow solid without further purifications. The catalyst was filtered off on a CELITE™ pad the filter cake was washed with ethanol The filtrate was evaporated under reduced pressure

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A 2 L round bottomed flask was charged with 23 g (116 mmol) 2-methoxy-1,3-dinitrobenzene and 261 g (1.16 mol) tin chloride dihydrate. 160 mL EtOH was added, and the resulting suspension was stirred at 70° C. for 90 min. In the beginning, the reaction is very exothermic be careful! The solvent was removed and the reaction mixture was diluted with H2O and slowly added to about 500 mL of a 10 M NaOH solution. The suspension was cooled down to RT and extracted three times with EtOAc. The combined organic layers were dried over MgSO4, filtered and the solvent was removed under reduced pressure. The product was obtained as red oil and used without further purification. The solvent was removed the reaction mixture was diluted with H2O slowly added to about 500 mL of a 10 M NaOH solution The suspension was cooled down to RT extracted three times with EtOAc The combined organic layers were dried over MgSO4 filtered the solvent was removed under reduced pressure The product was obtained as red oil used without further purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 0.500 g (2.52 mmol) of compound 2,6-dinitroanisole was suspended in 40 mL of water together with 2.310 g (35.3 mmol) of Zn and 0.530 g (10.1 mmol) of NH4Cl. The solution was boiled for 2.5 h. After cooling to room temperature, the solution was extracted with ethyl acetate. The organic solution was dried with anhydrous Na2SO4 and distilled in vacuo to obtain 0.330 g (95%) of clean 2,6-diaminoanisole as a red oil. 1H NMR (CDCl3) δ 6.73 (t, J=7.9 Hz, 1H, Ar—H), 6.19 (d, J=7.9 Hz, 2H, Ar—H), 3.78 (s, 3H, O—CH3), 3.73 (br. s, 4H, Ar—NH2). 13C NMR (CDCl3) δ 140.3, 134.9, 125.2, 106.6, 58.6. the solution was extracted with ethyl acetate The organic solution was dried with anhydrous Na2SO4 distilled in vacuo