2-chloro-3-oxo-N-phenylbutanamide

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

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

Procedure: 52.9 g of α-chloroacetoacetanilide in 500 ml of methylene chloride was held at 0° C for 4 hours and then 725 ml of methylene chloride solution titrating 17.4 g/l of diazomethane were added. The mixture was stirred for 16 hours at 0° C and then 1 hour at 20° C and was concentrated to dryness under reduced pressure. The residue was added to isopropyl ether and the precipitate formed was recovered by vacuum filtration and was crystallized from isopropyl ether to obtain 12 g of 2-chloro-3-methoxy-crotonanilide melting at 100° C. were added 1 hour at 20° C and was concentrated to dryness under reduced pressure The residue was added to isopropyl ether the precipitate formed was recovered by vacuum filtration was crystallized from isopropyl ether

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

Procedure: 52.9 g of α-chloroacetoacetanilide in 500 ml of methylene chloride was held at 0° C for 4 hours and then 725 ml of methylene chloride solution titrating 17.4 g/l of diazomethane were added. The mixture was stirred for 16 hours at 0° C and then 1 hour at 20° C and was concentrated to dryness under reduced pressure. The residue was added to isopropyl ether and the precipitate formed was recovered by vacuum filtration and was crystallized from isopropyl ether to obtain 12 g of 2-chloro-3-methoxy-crotonanilide melting at 100° C. were added 1 hour at 20° C and was concentrated to dryness under reduced pressure The residue was added to isopropyl ether the precipitate formed was recovered by vacuum filtration was crystallized from isopropyl ether

Conditions: temp:6.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A suspension of 177 g (1.0 mole) of acetoacetanilide in 1440 ml of toluene and 167 ml of water, in a chlorinator (2000 ml 3-neck flask), was cooled to approximately 6° C. and chlorine gas was added at about the rate of 1.5 g/minute, while maintaining the temperature at 6° C. until 82.6 g (1.16 moles) of chlorine had been added (about 56 minutes). The resultant mixture was stirred for an additional 36 minutes and then heated to 70° C. for 15 minutes. The mixture was then cooled and the product was precipitated. The precipitate was filtered from the toluene/aqueous HCl mixture to give 134.8 g (63.9%) of α-chloroacetoacetanilide, mp 132°-134° C. had been added (about 56 minutes) heated to 70° C. for 15 minutes The mixture was then cooled the product was precipitated The precipitate was filtered from the toluene/aqueous HCl mixture

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

Procedure: 52.9 g of α-chloroacetoacetanilide in 500 ml of methylene chloride was held at 0° C for 4 hours and then 725 ml of methylene chloride solution titrating 17.4 g/l of diazomethane were added. The mixture was stirred for 16 hours at 0° C and then 1 hour at 20° C and was concentrated to dryness under reduced pressure. The residue was added to isopropyl ether and the precipitate formed was recovered by vacuum filtration and was crystallized from isopropyl ether to obtain 12 g of 2-chloro-3-methoxy-crotonanilide melting at 100° C. were added 1 hour at 20° C and was concentrated to dryness under reduced pressure The residue was added to isopropyl ether the precipitate formed was recovered by vacuum filtration was crystallized from isopropyl ether