2-(2-aminophenoxy)ethanol

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

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g (39.17 mmol) 2-(2-hydroxyethoxy)aniline A3, 5 ml (5.85 g, 47 mmol) 2-(2-chloroethoxy)ethanol and 8.19 ml (5.95 g, 58.75 mmol) triethylamine were dissolved in 20 ml dimethylformamide and stirred for 4 days at 90° C. After cooling, the solution was filtered, the precipitate washed with dichioromethane and the filtrate concentrated in vacuo. The residue was taken up in chloroform and washed twice with a small quantity of water. The chloroform solution was then dried over sodium sulfate and concentrated. The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase. 5 g of brown, viscous oil were obtained; yield 53%. After cooling the solution was filtered the precipitate washed with dichioromethane the filtrate concentrated in vacuo washed twice with a small quantity of water The chloroform solution was then dried over sodium sulfate concentrated The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase 5 g of brown, viscous oil were obtained

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.9 g (48.59 mmol) 2-(2-hydroxyethoxy)nitrobenzene A2, 16.44 g (72.88 mmol) SnCl2 ·2H2O and 17.3 g (145.77 mmol) tin were stirred in 30.84 ml aqueous HCl (30%) and 25 ml water at 90° C. for 8 hours. After cooling, the solution was treated with aqueous 5n sodium hydroxide solution and stirred for 3 hours at 90° C. The aqueous solution was subsequently decanted, wherein, upon cooling, the crude product crystallized out and was removed by suction. This crude product was then taken up in methanol, warmed and the suspension was filtered. The filtrate was then concentrated in vacuo. 6 g of light-brown crystals were obtained; yield 80%. After cooling The aqueous solution was subsequently decanted wherein, upon cooling the crude product crystallized out was removed by suction warmed the suspension was filtered The filtrate was then concentrated in vacuo

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.9 g (48.59 mmol) 2-(2-hydroxyethoxy)nitrobenzene A2, 16.44 g (72.88 mmol) SnCl2 ·2H2O and 17.3 g (145.77 mmol) tin were stirred in 30.84 ml aqueous HCl (30%) and 25 ml water at 90° C. for 8 hours. After cooling, the solution was treated with aqueous 5n sodium hydroxide solution and stirred for 3 hours at 90° C. The aqueous solution was subsequently decanted, wherein, upon cooling, the crude product crystallized out and was removed by suction. This crude product was then taken up in methanol, warmed and the suspension was filtered. The filtrate was then concentrated in vacuo. 6 g of light-brown crystals were obtained; yield 80%. After cooling The aqueous solution was subsequently decanted wherein, upon cooling the crude product crystallized out was removed by suction warmed the suspension was filtered The filtrate was then concentrated in vacuo

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

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g (39.17 mmol) 2-(2-hydroxyethoxy)aniline A3, 5 ml (5.85 g, 47 mmol) 2-(2-chloroethoxy)ethanol and 8.19 ml (5.95 g, 58.75 mmol) triethylamine were dissolved in 20 ml dimethylformamide and stirred for 4 days at 90° C. After cooling, the solution was filtered, the precipitate washed with dichloromethane and the filtrate concentrated in vacuo. The residue was taken up in chloroform and washed twice with a small quantity of water. The chloroform solution was then dried over sodium sulfate and concentrated. The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase. 5 g of brown, viscous oil were obtained; yield 53%. After cooling the solution was filtered the precipitate washed with dichloromethane the filtrate concentrated in vacuo washed twice with a small quantity of water The chloroform solution was then dried over sodium sulfate concentrated The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase 5 g of brown, viscous oil were obtained

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.9 g (48.59 mmol) 2-(2-hydroxyethoxy)nitrobenzene A2, 16.44 g (72.88 mmol) SnCl2. 2H2O and 17.3 g (145.77 mmol) tin were stirred in 30.84 ml aqueous HCl (30%) and 25 ml water at 90° C. for 8 hours. After cooling, the solution was treated with aqueous 5n sodium hydroxide solution and stirred for 3 hours at 90° C. The aqueous solution was subsequently decanted, wherein, upon cooling, the crude product crystallized out and was removed by suction. This crude product was then taken up in methanol, warmed and the suspension was filtered. The filtrate was then concentrated in vacuo. 6 g of light-brown crystals were obtained; yield 80%. After cooling The aqueous solution was subsequently decanted wherein, upon cooling the crude product crystallized out was removed by suction warmed the suspension was filtered The filtrate was then concentrated in vacuo

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6 g (39.17 mmol) 2-(2-hydroxyethoxy)aniline A3, 5 ml (5.85 g, 47 mmol) 2-(2-chloroethoxy)ethanol and 8.19 ml (5.95 g, 58.75 mmol) triethylamine were dissolved in 20 ml dimethylformamide and stirred for 4 days at 90° C. After cooling, the solution was filtered, the precipitate washed with dichioromethane and the filtrate concentrated in vacuo. The residue was taken up in chloroform and washed twice with a small quantity of water. The chloroform solution was then dried over sodium sulfate and concentrated. The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase. 5 g of brown, viscous oil were obtained; yield 53%. After cooling the solution was filtered the precipitate washed with dichioromethane the filtrate concentrated in vacuo washed twice with a small quantity of water The chloroform solution was then dried over sodium sulfate concentrated The viscous crude product was purified by column chromatography on silica gel 60 with toluene/acetone 1:2 as the mobile phase 5 g of brown, viscous oil were obtained

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.9 g (48.59 mmol) 2-(2-hydroxyethoxy)nitrobenzene A2, 16.44 g (72.88 mmol) SnCl2 ·2H2O and 17.3 g (145.77 mmol) tin were stirred in 30.84 ml aqueous HCl (30%) and 25 ml water at 90° C. for 8 hours. After cooling, the solution was treated with aqueous 5n sodium hydroxide solution and stirred for 3 hours at 90° C. The aqueous solution was subsequently decanted, wherein, upon cooling, the crude product crystallized out and was removed by suction. This crude product was then taken up in methanol, warmed and the suspension was filtered. The filtrate was then concentrated in vacuo. 6 g of light-brown crystals were obtained; yield 80%. After cooling The aqueous solution was subsequently decanted wherein, upon cooling the crude product crystallized out was removed by suction warmed the suspension was filtered The filtrate was then concentrated in vacuo