N-(2,3-dichlorophenyl)acetamide

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

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

Procedure: Nitric acid (30 ml) is cooled to -5°, and N-methylcarbonyl 2,3-dichloroaniline (9.8 g, 48 mmol) is added to the acid in small portions, with the temperature maintained at -5° or lower. After the addition is complete, the reaction is stirred for 1 hour at +5°. The reaction is then added dropwise to about 150 g of ice-water mixture. The resulting solid is collected by filtration and purified by prep. TLC (developing with 30% ethyl acetate/hexane). The least polar component is isolated to give N-methylcarbonyl 2,3-dichloro-6-nitroaniline. maintained at -5° After the addition The resulting solid is collected by filtration purified by prep The least polar component is isolated

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

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

Procedure: To a solution 2.06 g (12.71 mmol) of 2,3-dichloroaniline (16-1) in 10 mL of benzene cooled in an ice bath was added drop wise a 10 mL benzene solution of 1.95 g (19.07 mmol) of acetic anhydride. The reaction mixture was then brought to reflux for 1 hour, cooled to room temperature and filtered off the desired product 16-2. MS (M+1): theoretical 203.0; measured 204.1. 1H NMR (CDCl3): 2.26 (s, 3H), 7.21 (m, 2H), 7.68 (m, 1H), 8.33 (m, 1H). to reflux for 1 hour filtered off the desired product 16-2

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

Procedure: Nitric acid (30 ml) is cooled to -5°, and N-methylcarbonyl 2,3-dichloroaniline (9.8 g, 48 mmol) is added to the acid in small portions, with the temperature maintained at -5° or lower. After the addition is complete, the reaction is stirred for 1 hour at +5°. The reaction is then added dropwise to about 150 g of ice-water mixture. The resulting solid is collected by filtration and purified by prep. TLC (developing with 30% ethyl acetate/hexane). The least polar component is isolated to give N-methylcarbonyl 2,3-dichloro-6-nitroaniline. maintained at -5° After the addition The resulting solid is collected by filtration purified by prep The least polar component is isolated