BENZENAMINE, 4-ETHYL-3-METHOXY- synthesis

Yield:947691-59-0 72%

Reaction Conditions:

Stage #1: 2-ethyl-5-nitro-anisolewith ethanol;water;ammonium chloride;acetic acid;zinc at 0 - 20; for 3 h;
Stage #2: with sodium hydrogencarbonate in water; pH=7;

Steps:

1.5

Step 5. A mixture of ammonium chloride (15.2 g, 284.11 mmol) in water (100 mL) was added to a solution of l-ethyl-2-methoxy-4-nitrobenzene (5.15 g, 25.61 mmol, prepared as described above in step 4) in ethanol (100 mL). The mixture was cooled to 0-5 ⁰C and zinc (7.40 g, 113.85 mmol) was added in several portions. Acetic acid (6.83 g, 113.83 mmol) was then added dropwise at 0-5 ⁰C. The resulting solution was stirred at room temperature for 3 hr. The mixture was concentrated and sodium bicarbonate was added to adjust the pH to 7. The resulting solution was extracted with ethyl acetate and the organic layers were combined, washed with brine, dried (anhydrous MgSO_i), filtered, and concentrated. The residue was purified by eluting through a column with a 1:5 (v/v) ethyl acetate/petroleum ether solvent system to afford 3.1 g (72 % yield) of 4-ethyl-3-methoxy- benzenamine as a green solid.

References:

WO2007/103260,2007,A1 Location in patent:Page/Page column 57