3-oxo-N-phenylbutanamide

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

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

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

Procedure: Sodium hydride (0.48 g. of a 50% w/w dispersion in mineral oil) was added to a solution of 2-acetylacetanilide (1.8 g.) in dry dimethylformamide (15 ml.) under an atmosphere of argon. The mixture was stirred at 35° until the evolution of hydrogen had ceased. 2-Bromopropane (1.12 ml.) was added, and the mixture was heated at 55°-60° for 110 hr. The mixture was cooled and then poured into water (100 ml.). The resulting solution was adjusted to pH 2 with 3N-hydrochloric acid and extracted with ethyl acetate (3×100 ml.). The ethyl acetate extract was dried (Na2SO4) and the ethyl acetate was evaporated in vacuo. The residual oil was chromatographed on silica gel (Kieselgel 60, 180 g.) using 20% v/v ethyl acetate in petroleum ether (b.p. 60°-80°) as eluant. The relevant fraction was evaporated in vacuo, and the residue was crystallised from cyclohexane to give 2-acetyl-2-isopropylacetanilide, m.p. 135°-7° . the mixture was heated at 55°-60° for 110 hr The mixture was cooled extracted with ethyl acetate (3×100 ml.) The ethyl acetate extract was dried (Na2SO4) the ethyl acetate was evaporated in vacuo The residual oil was chromatographed on silica gel (Kieselgel 60, 180 g.) The relevant fraction was evaporated in vacuo the residue was crystallised from cyclohexane

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

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

Procedure: Under a nitrogen atmosphere, a solution of bromine (1.16 ml, 22.59 mmol) in 17 ml of acetic acid containing a small crystal of iodine was added over 2.5 hours to a solution of acetoacetanilide (4.0 g, 22.57 mmol) in 12 ml of acetic acid, at room temperature (cooling with cold water). The reaction mixture was stirred at room temperature for 3 hours, then poured into 100 ml of ice-cold water and the crude solid product was filtered off. Following crystallization from ethanol, 3.30 g of 4-bromoacetoacetanilide were obtained, m.p 130°-132° C. the crude solid product was filtered off crystallization from ethanol

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Aminophenol-4-sulfonic acid (18 g) was dissolved in aqueous sodium hydroxide (5 g in 200 ml of water). After the addition of sodium nitrite (7 g), the solution was cooled to 10° C. and added to a mixture of concentrated hydrochloric acid (25 ml) and cracked ice (300 g). The diazonium solution was stirred at 0° C. for 15 minutes and then added slowly to a slurry of acetoacetanilide (17 g), potassium carbonate (30 g), pyridine (200 ml) and ice. When the addition was complete, the reaction mixture was stirred at 10° to 20° C. for 1 hour and then acidified with hydrochloric acid. The product was filtered off and dried. When the addition The product was filtered off dried

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Aminophenol-4-sulfonic acid (18 g) was dissolved in aqueous sodium hydroxide (5 g in 200 ml of water). After the addition of sodium nitrite (7 g), the solution was cooled to 10° C. and added to a mixture of concentrated hydrochloric acid (25 ml) and cracked ice (300 g). The diazonium solution was stirred at 0° C. for 15 minutes and then added slowly to a slurry of acetoacetanilide (17 g), potassium carbonate (30 g), pyridine (200 ml) and ice. When the addition was complete, the reaction mixture was stirred at 10° to 20° C. for 1 hour and then acidified with hydrochloric acid. The product was filtered off and dried. When the addition The product was filtered off dried

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetoacetanilide was mixed with phenyl glycidyl ether in a molar ratio of 1:1.2, and a reaction was allowed to proceed by heating the mixture at 170° C. for 1 hour. Then, the remaining unreacted phenyl glycidyl ether was removed in the same manner as in Reference Example 1, thereby obtaining a reaction product, (D)-2. Reaction product (D)-2 was further subjected to infrared spectrophotometry and gel permeation chromatography in the same manner as in Reference Example 1. This reaction product (D)-2 was a mixture containing, besides the desired compound formed by the reaction of the 1:1 reactants, high molecular weiqht compounds formed through further reactions. Then, the remaining unreacted phenyl glycidyl ether was removed in the same manner as in Reference Example 1 obtaining a reaction product Reaction product (D)-2

Conditions: temp:170.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Acetoacetanilide was mixed with phenyl glycidyl ether in a molar ratio of 1:1.2, and a reaction was allowed to proceed by heating the mixture at 170° C. for 1 hour. Then, the remaining unreacted phenyl glycidyl ether was removed in the same manner as in Reference Example 1, thereby obtaining a reaction product, (D)-2. Reaction product (D)-2 was further subjected to infrared spectrophotometry and gel permeation chromatography in the same manner as in Reference Example 1. This reaction product (D)-2 was a mixture containing, besides the desired compound formed by the reaction of the 1:1 reactants, high molecular weiqht compounds formed through further reactions. Then, the remaining unreacted phenyl glycidyl ether was removed in the same manner as in Reference Example 1 obtaining a reaction product Reaction product (D)-2

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

Procedure: A solution of 24 parts of α-acetoxypropionaldehyde, 35.4 parts of acetoacetanilide and 2 parts of p-toluenesulfonic acid in 100 parts of benzene is kept for 3 hours at 40° C and then boiled under reflux for 1 hour. Adopting the isolation procedure described in Example 1 there is obtained 41.8 parts of 2,5-dimethylfuran-3-carboxanilide having a melting point of 92° to 93° C. under reflux for 1 hour

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

Procedure: Acetoacetanilide (25.0 g, 0.14 mol) and sodium nitrite (12.65 g, 0.18 mol) were dissolved in aqueous sodium hydroxide solution (140 ml, 1 N) and the resulting solution was added dropwise over 20 min to an aqueous solution of sulfuric acid (120 ml conc. H2SO4 in 950 ml water) cooled in an ice bath. The reaction mixture was stirred at 0° C. for 30 min, then the precipitate was filtered and washed with water to yield 2-hydroxyiminoacetanilide (22.64 g., 78% yield) as a pale yellow solid. cooled in an ice bath the precipitate was filtered washed with water

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

Procedure: Acetoacetanilide (25.0 g, 0.14 mol) and sodium nitrite (12.65 g, 0.18 mol) were dissolved in aqueous sodium hydroxide solution (140 ml, 1 N) and the resulting solution was added dropwise over 20 min to an aqueous solution of sulfuric acid (120 ml conc. H2SO4 in 950 ml water) cooled in an ice bath. The reaction mixture was stirred at 0° C. for 30 min, then the precipitate was filtered and washed with water to yield 2-hydroxyiminoacetanilide (22.64 g., 78% yield) as a pale yellow solid. cooled in an ice bath the precipitate was filtered washed with water