N-(2-chlorophenyl)-3-oxobutanamide

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 1.46 g (20 m mol) of n-butylamine and 20 ml of toluene, after one drop of acetic acid was added, was stirred for 1.5 hours at 60° C. and was refluxed for 30 minutes while resulted water was distilled off from the reaction mixture together with about 10 ml of toluene. After 8.10 g (80 m mol) of triethylamine was added, a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes and the reaction mixture was further refluxed for 2 hours. The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture and was cooled to room temperature. The resulting crystals were filtered off, washed and dried under reduced pressure to obtain 1.59 g of the title compound. (Yield: 29%). was refluxed for 30 minutes was distilled off from the reaction mixture together with about 10 ml of toluene After 8.10 g (80 m mol) of triethylamine was added a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes the reaction mixture was further refluxed for 2 hours The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture was cooled to room temperature The resulting crystals were filtered off washed dried under reduced pressure

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 1.46 g (20 m mol) of n-butylamine and 20 ml of toluene, after one drop of acetic acid was added, was stirred for 1.5 hours at 60° C. and was refluxed for 30 minutes while resulted water was distilled off from the reaction mixture together with about 10 ml of toluene. After 8.10 g (80 m mol) of triethylamine was added, a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes and the reaction mixture was further refluxed for 2 hours. The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture and was cooled to room temperature. The resulting crystals were filtered off, washed and dried under reduced pressure to obtain 1.59 g of the title compound. (Yield: 29%). was refluxed for 30 minutes was distilled off from the reaction mixture together with about 10 ml of toluene After 8.10 g (80 m mol) of triethylamine was added a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes the reaction mixture was further refluxed for 2 hours The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture was cooled to room temperature The resulting crystals were filtered off washed dried under reduced pressure

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

Procedure: A mixture of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 2.55 g (20 m mol) of o-chloroaniline and 20 ml of toluene, after adding one drop of hydrochloric acid was refluxed for 2 hours while the resulted water was distilled off from the reaction system together with about 10 ml of toluene. After 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution, a solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes. was distilled off from the reaction system together with about 10 ml of toluene After 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution a solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes

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

Procedure: 8.62 g of p-chloro-o-nitroaniline, 10.89 g of acetoacet-o-chloroanilide, 2.36 g of α-chloroacetic acid and 50 ml of 2-ethylhexanoic acid are stirred at 600 rpm for 1 hour in a 1/2 liter grinding pot containing 200 g of 2-3 mm diameter glass beads. The temperature reaches 26° C. 4.14 g of sodium nitrite are added and stirring continued. As pigment formation commences and the grinding viscosity increases, 25 ml portions of 2-ethylhexanoic acid are added after 2 and 5 minutes. A maximum temperature of 36° C. is obtained after 16 minutes, and after 1 hour, at a temperature of 32° C., aqueous ammonia solution is added and the pigment product recovered, washing well with hot water at the filtration stage. The C.I. Pigment Yellow 3 product, obtained in a yield of 17.84 g (90.3% of theory) is approximately 20% stronger and slightly redder than the corresponding product prepared by conventional aqueous coupling, when dispersed in a decorative alkyd paint system. grinding pot containing 200 g of 2-3 mm diameter glass beads reaches 26° C As pigment formation commences and the grinding viscosity increases A maximum temperature of 36° C. is obtained after 16 minutes the pigment product recovered washing well with hot water at the filtration stage

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

Procedure: 8.62 g of p-chloro-o-nitroaniline, 10.89 g of acetoacet-o-chloroanilide, 2.36 g of α-chloroacetic acid and 50 ml of 2-ethylhexanoic acid are stirred at 600 rpm for 1 hour in a 1/2 liter grinding pot containing 200 g of 2-3 mm diameter glass beads. The temperature reaches 26° C. 4.14 g of sodium nitrite are added and stirring continued. As pigment formation commences and the grinding viscosity increases, 25 ml portions of 2-ethylhexanoic acid are added after 2 and 5 minutes. A maximum temperature of 36° C. is obtained after 16 minutes, and after 1 hour, at a temperature of 32° C., aqueous ammonia solution is added and the pigment product recovered, washing well with hot water at the filtration stage. The C.I. Pigment Yellow 3 product, obtained in a yield of 17.84 g (90.3% of theory) is approximately 20% stronger and slightly redder than the corresponding product prepared by conventional aqueous coupling, when dispersed in a decorative alkyd paint system. grinding pot containing 200 g of 2-3 mm diameter glass beads reaches 26° C As pigment formation commences and the grinding viscosity increases A maximum temperature of 36° C. is obtained after 16 minutes the pigment product recovered washing well with hot water at the filtration stage

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

Procedure: 8.62 g of p-chloro-o-nitroaniline, 10.89 g of acetoacet-o-chloroanilide, 2.36 g of α-chloroacetic acid and 50 ml of 2-ethylhexanoic acid are stirred at 600 rpm for 1 hour in a 1/2 liter grinding pot containing 200 g of 2-3 mm diameter glass beads. The temperature reaches 26° C. 4.14 g of sodium nitrite are added and stirring continued. As pigment formation commences and the grinding viscosity increases, 25 ml portions of 2-ethylhexanoic acid are added after 2 and 5 minutes. A maximum temperature of 36° C. is obtained after 16 minutes, and after 1 hour, at a temperature of 32° C., aqueous ammonia solution is added and the pigment product recovered, washing well with hot water at the filtration stage. The C.I. Pigment Yellow 3 product, obtained in a yield of 17.84 g (90.3% of theory) is approximately 20% stronger and slightly redder than the corresponding product prepared by conventional aqueous coupling, when dispersed in a decorative alkyd paint system. grinding pot containing 200 g of 2-3 mm diameter glass beads reaches 26° C As pigment formation commences and the grinding viscosity increases A maximum temperature of 36° C. is obtained after 16 minutes the pigment product recovered washing well with hot water at the filtration stage

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

Procedure: To a mixture of N-(2-chlorophenyl)-3-oxobutanamide (2.63 g), potassium carbonate (1.72 g) and N,N-dimethylformamide (31.0 mL) was added dropwise 1,1-dimethoxy-N,N-dimethylmethanamine (3.30 mL) over 30 min at room temperature, and the reaction mixture was stirred at room temperature for 2 hr. The reaction mixture was slowly poured into water, and the mixture was extracted with dichloromethane. The extract was washed with water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.30 g). the mixture was extracted with dichloromethane The extract was washed with water dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 1.46 g (20 m mol) of n-butylamine and 20 ml of toluene, after one drop of acetic acid was added, was stirred for 1.5 hours at 60° C. and was refluxed for 30 minutes while resulted water was distilled off from the reaction mixture together with about 10 ml of toluene. After 8.10 g (80 m mol) of triethylamine was added, a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes and the reaction mixture was further refluxed for 2 hours. The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture and was cooled to room temperature. The resulting crystals were filtered off, washed and dried under reduced pressure to obtain 1.59 g of the title compound. (Yield: 29%). was refluxed for 30 minutes was distilled off from the reaction mixture together with about 10 ml of toluene After 8.10 g (80 m mol) of triethylamine was added a solution of 4.20 g (50 m mol) of diketene in 20 ml of toluene was dropwise added over a period of 40 minutes the reaction mixture was further refluxed for 2 hours The reaction mixture was heated to distill off about 12 ml of solvent from the reaction mixture was cooled to room temperature The resulting crystals were filtered off washed dried under reduced pressure

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

Procedure: A mixture of 4.23 g (20 m mol) of o-chloroacetoacetanilide, 2.55 g (20 m mol) of o-chloroaniline and 20 ml of toluene, after adding one drop of hydrochloric acid was refluxed for 2 hours while the resulted water was distilled off from the reaction system together with about 10 ml of toluene. After 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution, a solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes. was distilled off from the reaction system together with about 10 ml of toluene After 9.30 g (80 m mol) of N,N,N',N'-tetramethylethylenediamine was added to the remaining solution a solution of 9.94 g (70 m mol) of 2,2,6-trimethyl-4H-1,3-dioxin-4-one in 25 ml of toluene was dropwise added over a period of 15 minutes