(3,5-dichloro-4-methoxyphenyl)methanamine

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

Procedure: A mixture of 3,5-dichloro-4-methoxybenzylamine (6 g, 29.2 mmole), 2-fluoronitrobenzene (2 g, 14.2 mmole) and ammonium acetate (1.0 g) was heated at 80° for 1 hour. The cooled mixture was taken up into ethyl acetate and washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine, dried (Na2SO4), and concentrated to give the title compound 4.0 g (78%) as orange crystals, mp 128°. was heated at 80° for 1 hour washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine dried (Na2SO4) concentrated

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

Procedure: A solution of 3,5-dichloro-4-methoxybenzaldehyde methoxime (10.7 g, 46 mmol) in freshly distilled tetrahydrofuran (THF) (60 ml) was cooled to 0° and stirred while 47 ml of 0.98M borane in THF was added. The resulting mixture was heated under reflux for 2 hours, cooled, and water (20 ml) added followed by 20% aqueous sodium hydroxide (20 ml). The mixture was heated under reflux for 2 hours, cooled and extracted twice with diethyl ether. The organic layer was extracted with 3N HCl, the aqueous layer made basic with 50% aqueous sodium hydroxide and the product was extracted into diethyl ether. The organic extracts were dried (Na2SO4) and concentrated to give 6.11 g (65%) of the title compound as a pale yellow oil. was added The resulting mixture was heated under reflux for 2 hours cooled The mixture was heated under reflux for 2 hours cooled extracted twice with diethyl ether The organic layer was extracted with 3N HCl the product was extracted into diethyl ether The organic extracts were dried (Na2SO4) concentrated

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

Procedure: A solution of 3,5-dichloro-4-methoxybenzaldehyde methoxime (10.7 g, 46 mmol) in freshly distilled tetrahydrofuran (THF) (60 ml) was cooled to 0° and stirred while 47 ml of 0.98M borane in THF was added. The resulting mixture was heated under reflux for 2 hours, cooled, and water (20 ml) added followed by 20% aqueous sodium hydroxide (20 ml). The mixture was heated under reflux for 2 hours, cooled and extracted twice with diethyl ether. The organic layer was extracted with 3N HCl, the aqueous layer made basic with 50% aqueous sodium hydroxide and the product was extracted into diethyl ether. The organic extracts were dried (Na2SO4) and concentrated to give 6.11 g (65%) of the title compound as a pale yellow oil. was added The resulting mixture was heated under reflux for 2 hours cooled The mixture was heated under reflux for 2 hours cooled extracted twice with diethyl ether The organic layer was extracted with 3N HCl the product was extracted into diethyl ether The organic extracts were dried (Na2SO4) concentrated

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

Procedure: A mixture of 3,5-dichloro-4-methoxybenzylamine (6 g, 29.2 mmole), 2-fluoronitrobenzene (2 g, 14.2 mmole) and ammonium acetate (1.0 g) was heated at 80° for 1 hour. The cooled mixture was taken up into ethyl acetate and washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine, dried (Na2SO4), and concentrated to give the title compound 4.0 g (78%) as orange crystals, mp 128°. was heated at 80° for 1 hour washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine dried (Na2SO4) concentrated

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

Procedure: A solution of 3,5-dichloro-4-methoxybenzaldehyde methoxime (10.7 g, 46 mmol) in freshly distilled tetrahydrofuran (THF) (60 ml) was cooled to 0° and stirred while 47 ml of 0.98M borane in THF was added. The resulting mixture was heated under reflux for 2 hours, cooled, and water (20 ml) added followed by 20% aqueous sodium hydroxide (20 ml). The mixture was heated under reflux for 2 hours, cooled and extracted twice with diethyl ether. The organic layer was extracted with 3N HCl, the aqueous layer made basic with 50% aqueous sodium hydroxide and the product was extracted into diethyl ether. The organic extracts were dried (Na2SO4) and concentrated to give 6.11 g (65%) of the title compound as a pale yellow oil. was added The resulting mixture was heated under reflux for 2 hours cooled The mixture was heated under reflux for 2 hours cooled extracted twice with diethyl ether The organic layer was extracted with 3N HCl the product was extracted into diethyl ether The organic extracts were dried (Na2SO4) concentrated

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

Procedure: A mixture of 3,5-dichloro-4-methoxybenzylamine (6 g, 29.2 mmole), 2-fluoronitrobenzene (2 g, 14.2 mmole) and ammonium acetate (1.0 g) was heated at 80° for 1 hour. The cooled mixture was taken up into ethyl acetate and washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine, dried (Na2SO4), and concentrated to give the title compound 4.0 g (78%) as orange crystals, mp 128°. was heated at 80° for 1 hour washed sequentially with aqueous 3N HCl, water, aqueous 5% sodium bicarbonate, brine dried (Na2SO4) concentrated

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

Procedure: A solution of 3,5-dichloro-4-methoxybenzaldehyde methoxime (10.7 g, 46 mmol) in freshly distilled tetrahydrofuran (THF) (60 ml) was cooled to 0° and stirred while 47 ml of 0.98M borane in THF was added. The resulting mixture was heated under reflux for 2 hours, cooled, and water (20 ml) added followed by 20% aqueous sodium hydroxide (20 ml). The mixture was heated under reflux for 2 hours, cooled and extracted twice with diethyl ether. The organic layer was extracted with 3N HCl, the aqueous layer made basic with 50% aqueous sodium hydroxide and the product was extracted into diethyl ether. The organic extracts were dried (Na2SO4) and concentrated to give 6.11 g (65%) of the title compound as a pale yellow oil. was added The resulting mixture was heated under reflux for 2 hours cooled The mixture was heated under reflux for 2 hours cooled extracted twice with diethyl ether The organic layer was extracted with 3N HCl the product was extracted into diethyl ether The organic extracts were dried (Na2SO4) concentrated