1-(5-amino-2-hydroxyphenyl)ethanone

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

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

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirring solution of 1-(5-amino-2-hydroxy-phenyl)-ethanone (6.856 g,46 mmol) in 98% sulfuric acid (24 ml) and water (19 ml) was added sodium nitrite (3.30 g, 48 mmol, 1.05 equ) in water (5.5 ml). The reaction was stirred for 35 minutes, then sulfuric acid (4 ml), copper powder (0.17 g, 0.3 mmol, 0.06 equ) and potassium iodide (8.80 g, 53 mmol, 1.16 equ) in water (5.5 ml) added. The mixture was then heated slowly to 65° C. and maintained at 65° C. for 2 hours. The reaction was then cooled, water (25 ml) and sodium hydrogen carbonate added. More water was added, then extracted into a mixture of ethyl acetate and dichloromethane, then ethyl acetate (2×). The combined organic layers were washed with brine then concentrated in vacuo. This mixture was then taken up in ethyl acetate and 2 M HCl, filtered and the organic layer dried (MgSO4) and concentrated in vacuo to give 1-(5-iodo-2-hydroxy-phenyl)-ethanone 52 (1.339 g, 39%) as a purple oil. This was then used in the next reaction. maintained at 65° C. for 2 hours The reaction was then cooled extracted into a mixture of ethyl acetate and dichloromethane The combined organic layers were washed with brine then concentrated in vacuo 2 M HCl, filtered the organic layer dried (MgSO4) concentrated in vacuo

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

Procedure: A suspension of N-(3-acetyl-4-hydroxy-phenyl)-acetamide (1.029 g, 5.3 mmol) in 15% HCl (1.5 ml, 6.2 mmol, 1.2 equ) was heated to reflux for 40 minutes, then cooled and neutralised with 10% aqueous ammonia. The precipitated solid was collected by filtration as 1-(5-amino-2-hydroxy-phenyl)-ethanone (0.677 g, 84%) a green solid. was heated to reflux for 40 minutes The precipitated solid was collected by filtration as 1-(5-amino-2-hydroxy-phenyl)-ethanone (0.677 g, 84%) a green solid