3-(1-aminoethyl)phenol

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

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

Procedure: 1-(3-Hydroxyphenyl)ethanone oxime (1.2 g; 7.9 mmol) was dissolved in methanol (20 mL), degassed with nitrogen. 10% Palladium on carbon (0.1 g) and conc. HCl (100 uL, 3 mmol) were added. The reaction was shaken under Parr shaker at 50 Psi for 5 h. The reaction was filtered and concentrated under reduced pressure to give crude 3-(1-aminoethyl)phenol (1.0 g, 100%) as a yellow oil. Analytical LCMS (M+H)+: m/z=138.0. degassed with nitrogen The reaction was filtered concentrated under reduced pressure

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

Conditions: temp:77.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 1000 ml of methanolic ammonia, 100 g of 3-hydroxyacetophenone, 25 g of molecular sieves and 10 g of Raney nickel was taken in an autoclave flask at 0-5° C. The autoclave flask was then closed and stirred for 6 h at 75-80° C. without applying hydrogen gas pressure. The reaction mass was further hydrogenated at 75-80° C. by applying 15-20 kg/cm2 pressure of hydrogen gas and the reaction mixture was allowed to stir while maintaining the same conditions of temperature and pressure for 18-22 h. After the completion of the reaction, the reaction mixture was cooled to room temperature and filtered through hyflo bed. The hyflo bed was washed with 200 ml methanol and the solvent distilled off, under reduced pressure at a temperature of 60° C. The reaction mass was cooled to 0-5° C. and stirred for 1 h to obtain a slurry. The solid thus obtained was filtered, washed with ethyl acetate and dried to obtain the title compound. was taken in an autoclave flask at 0-5° C The autoclave flask was then closed was further hydrogenated at 75-80° C. to stir while maintaining the same conditions of temperature and pressure for 18-22 h After the completion of the reaction the reaction mixture was cooled to room temperature filtered through hyflo bed The hyflo bed was washed with 200 ml methanol the solvent distilled off, under reduced pressure at a temperature of 60° C The reaction mass was cooled to 0-5° C. stirred for 1 h to obtain a slurry The solid thus obtained was filtered washed with ethyl acetate dried

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

Procedure: To a solution of 3-methyl-thiophene-2,5-dicarboxylic acid 2-methyl ester (0.1 g, 0.5 mmol) and 3-(1-amino-ethyl)-phenol (82 mg, 0.6 mmol) in DMF (4 ml) was added at rt triethylamine (0.1 ml, 0.75 mmol), HOBT (81 mg, 0.6 mmol) and HBTU (228 mg, 0.6 mmol). The mixture was stirred at rt for 30 min, then quenched with 1NHCl and extracted with EtOAc. The layers were separated. The organic layer was washed with brine, then dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography with 30-70% EtOAc in hexane to afford the desired product (121 mg, 75% yield). quenched with 1NHCl and extracted with EtOAc The layers were separated The organic layer was washed with brine dried over Na2SO4 concentrated under reduced pressure The residue was purified by flash chromatography with 30-70% EtOAc in hexane

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

Procedure: 1-(3-Hydroxyphenyl)ethanone oxime (1.2 g; 7.9 mmol) was dissolved in methanol (20 mL), degassed with nitrogen. 10% Palladium on carbon (0.1 g) and conc. HCl (100 uL, 3 mmol) were added. The reaction was shaken under Parr shaker at 50 Psi for 5 h. The reaction was filtered and concentrated under reduced pressure to give crude 3-(1-aminoethyl)phenol (1.0 g, 100%) as a yellow oil. Analytical LCMS (M+H)+: m/z=138.0. degassed with nitrogen The reaction was filtered concentrated under reduced pressure