3-N-propan-2-yl-4-propan-2-yloxybenzene-1,3-diamine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suspension of 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (385 mg, 1.62 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.162 mmol, 0.10 equiv) and air was evacuated with vacuum. The vacuum was replaced with a balloon filled with hydrogen gas, and the reaction was allowed to stir for 2 hours. The catalyst was filtered off using a pad of celite and rinsed with ethanol. The filtrate was concentrated, and the crude product was purified by flash chromatography and eluted with hexane:EtOAc=100:0 to 50:50 using 5% EtOAc increments to give 6-isopropoxy-N1-isopropylbenzene-1,3-diamine 31 (263 mg, 78%) as a solid. was evacuated with vacuum filled with hydrogen gas The catalyst was filtered off rinsed with ethanol The filtrate was concentrated the crude product was purified by flash chromatography eluted with hexane

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

Procedure: A suspension of 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (385 mg, 1.62 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.162 mmol, 0.10 equiv) and air was evacuated with vacuum. The vacuum was replaced with a balloon filled with hydrogen gas, and the reaction was allowed to stir for 2 hours. The catalyst was filtered off using a pad of celite and rinsed with ethanol. The filtrate was concentrated, and the crude product was purified by flash chromatography and eluted with hexane:EtOAc=100:0 to 50:50 using 5% EtOAc increments to give 6-isopropoxy-N1-isopropylbenzene-1,3-diamine 31 (263 mg, 78%) as a solid. was evacuated with vacuum filled with hydrogen gas The catalyst was filtered off rinsed with ethanol The filtrate was concentrated the crude product was purified by flash chromatography eluted with hexane

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A suspension of 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (385 mg, 1.62 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.162 mmol, 0.10 equiv) and air was evacuated with vacuum. The vacuum was replaced with a balloon filled with hydrogen gas, and the reaction was allowed to stir for 2 hours. The catalyst was filtered off using a pad of celite and rinsed with ethanol. The filtrate was concentrated, and the crude product was purified by flash chromatography and eluted with hexane:EtOAc=100:0 to 50:50 using 5% EtOAc increments to give 6-isopropoxy-N1-isopropylbenzene-1,3-diamine 31 (263 mg, 78%) as a solid. was evacuated with vacuum filled with hydrogen gas The catalyst was filtered off rinsed with ethanol The filtrate was concentrated the crude product was purified by flash chromatography eluted with hexane

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

Procedure: A suspension of 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (385 mg, 1.62 mmol, 1 equiv) in ethanol (3 mL) was charged with 10% Pd/C (50% water, 253 mg, 0.162 mmol, 0.10 equiv) and air was evacuated with vacuum. The vacuum was replaced with a balloon filled with hydrogen gas, and the reaction was allowed to stir for 2 hours. The catalyst was filtered off using a pad of celite and rinsed with ethanol. The filtrate was concentrated, and the crude product was purified by flash chromatography and eluted with hexane:EtOAc=100:0 to 50:50 using 5% EtOAc increments to give 6-isopropoxy-N1-isopropylbenzene-1,3-diamine 31 (263 mg, 78%) as a solid. was evacuated with vacuum filled with hydrogen gas The catalyst was filtered off rinsed with ethanol The filtrate was concentrated the crude product was purified by flash chromatography eluted with hexane

Conditions: temp:0.00; pressure:0.00; stir: