1-(4-amino-3-chlorophenyl)ethanone

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of sodium nitrite (1.63 g) in water (4.3 ml) was added dropwise to a solution of 4'-amino-3'-chloroacetophenone (2.5 g) and concentrated hydrochloric acid (5.5 ml) in water (5.5 ml) at 0° to 3° C., and the solution was stirred for 15 minutes at 0° C. The resulting solution was added portionwise to a mixture of sodium nitrite (7.3 g) and cuprous oxide (0.76 g) in water (32 ml) at -5° to 0° C. The mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature, and extracted with chloroform. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (60 g) eluting with chloroform. The fractions containing the desired compound were combined and concentrated under reduced pressure to give pale yellow crystals of 3'-chloro-4'-nitroacetophenone (2.2 g). The mixture was stirred for 1 hour at 0° C. and for 1 hour at room temperature extracted with chloroform The extract was washed with a saturated aqueous solution of sodium chloride dried over magnesium sulfate concentrated under reduced pressure eluting with chloroform The fractions containing the desired compound concentrated under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of p-aminoacetophenone (20 g), pyridine (11.7 g), and iodobenzene dichloride (40 g) in tetrahydrofuran (300 ml) was stirred for 5 hours at 0° C. The insoluble materials were filtered, and the filtrate was concentrated under reduced pressure. The residue obtained was crystallized from ethanol to give colorless crystals of 4'-amino-3'-chloroacetophenone (20.1 g). The insoluble materials were filtered the filtrate was concentrated under reduced pressure The residue obtained was crystallized from ethanol