3-[(4-methoxyphenyl)methoxy]aniline

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

Procedure: Fe (5.6 g, 100.28 mmol) was mixed with methanol:H2O (15 ml:3 ml) and refluxed for 30 minutes. After the temperature is dropped to room temperature, 1-(4-methoxybenzyloxy)-3-nitrobenzene (1.3 g, 5.01 mmol) dissolved in 6 ml of methanol:H2O (5:1) was added and then refluxed for 15 hours. Fe was removed using cellite, then the reaction mixture was washed using methanol and concentrated under vacuum to remove the solvent. After extraction with 100 ml of saturated ammonium chloride+150 ml of dichloromethane, the organic layer was washed with water. The organic solvent was concentrated under vacuum to obtain the title compound (1.14 g, 99%). After the temperature is dropped to room temperature was added refluxed for 15 hours Fe was removed the reaction mixture was washed concentrated under vacuum to remove the solvent After extraction with 100 ml of saturated ammonium chloride+150 ml of dichloromethane the organic layer was washed with water The organic solvent was concentrated under vacuum

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

Procedure: A mixture of the aniline (Intermediate 87, 24.6 g, 107.3 mmol), sodium bicarbonate (13.5 g, 161 mmol) and methyl chloracetate (10.1 ml, 118 mmol) in acetonitrile (30 ml) was heated at 90°-100° for 48 h. Water (200 ml) was added and the mixture extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (2×100 ml) and brine (100 ml) before drying (Na2SO4) and evaporating in vacuo to leave the crude product as a peach solid. Trituration with ether-hexane (1:1) gave the title compound (Intermediate 88) as a flesh coloured solid (30.3 g; 94%), m.p. 79°-81°. was heated at 90°-100° for 48 h the mixture extracted with ethyl acetate (3×100 ml) The combined extracts were washed with water (2×100 ml) and brine (100 ml) before drying (Na2SO4) evaporating in vacuo to leave the crude product as a peach solid