Hydrochloric Acid → 4-Ethoxymethyl-2,6-dimethylaniline

反応式

[CH2:1]([O:3][CH2:4][C:5]1[CH:10]=[C:9]([CH3:11])[C:8]([N+:12]([O-])=O)=[C:7]([CH3:15])[CH:6]=1)[CH3:2].Cl>C(O)C.[Fe]>[CH2:1]([O:3][CH2:4][C:5]1[CH:6]=[C:7]([CH3:15])[C:8]([NH2:12])=[C:9]([CH3:11])[CH:10]=1)[CH3:2]

参加物

実験手順

To a solution of the product from Step B (10.0 g) in 50% aqueous ethanol (150 ml) is added iron powder (7.5 g) and concentrated hydrochloric acid (2.0 ml in 10 ml ethanol). The mixture is stirred mechanically at reflux for 2 hours. The solids are filtered hot, washed with ethanol and discarded. The filtrate is neutralized with sodium bicarbonate, evaporated to a residue and extracted with dichloromethane. The organic phase is treated with charcoal and a small amount of silica gel, dried, and evaporated to afford crude, syrupy 4-ethoxymethyl-2,6-dimethylaniline. The product could be purified further by silica gel chromatography [cyclohexane/ethyl acetate (19:1)] or used directly in the next step. Yield after chromatography is 4.8 g.