ethyl 3-(4-aminophenyl)-3-oxopropanoate

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 440 ml of acetonitrile was dissolved 146 g of ethyl p-aminobenzoylacetate, and 70 ml of acetic anhydride was added dropwise to the solution at 40° C. After reacting at 40° C. for 1 hour, 48.8 g of 80% hydrazine hydrate was added thereto dropwise. After heat generation subsided, the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour. The reaction mixture was cooled to 5° C., and the precipitated crystals were filtered to yield 148 g of 3-(4-acetylaminophenyl)-2-pyrazolin-5-one as gray crystals having a melting point of 254° to 258° C. was added dropwise to the solution at 40° C After heat generation the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour the precipitated crystals were filtered

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a mixture comprising 224 g of reduced iron, 13.4 g of ammonium chloride, 1 liter of isopropyl alcohol and 0.2 liter of water was added 237 g of ethyl p-nitrobenzoylacetate in small portions at a temperature between 50° C. and 70° C. with caution against heat generation. The mixture was allowed to react at 70° C. for 1 hour, followed by filtration. To the filtrate was added 1 liter of water, and crystals precipitated upon cooling to 5° C. were separated by filtration to obtain 172 g of ethyl p-aminobenzoylacetate as yellow crystals having a melting point of 82° to 84° C. against heat generation to react at 70° C. for 1 hour followed by filtration To the filtrate was added 1 liter of water, and crystals precipitated were separated by filtration

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 224 g of reduced iron, 13.4 g of ammonium chloride, 1,000 ml of isopropyl alcohol, and 200 ml of water was prepared, and then 237 g of ethyl p-nitrobenzoylacetate was added thereto in small amounts at temperatures ranging between 50° and 70° C. They were reacted at 70° C. for 1 hour and then the reaction solution was filtered. Then, 1,000 ml of water was added to the filtrate and cooled to 5° C., and crystals precipitated were collected by filtration to yield 172 g of yellow ethyl p-aminobenzoylacetate crystals, m.p., 82°-4° C. was prepared ranging between 50° and 70° C They were reacted at 70° C. for 1 hour the reaction solution was filtered Then, 1,000 ml of water was added to the filtrate crystals precipitated were collected by filtration

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

Procedure: Ethanol (3.6 g) and tetrahydrofuran (10 ml) were dropwise added to a solution of 2-chlorosulfonylbutyl chloride (14.4 g) and tetrahydrofuran (21 ml) while cooling with ice. After stirring at room temperature for 1 hour, ethyl p-aminobenzoylacetate (13.3 g), N,N-dimethylacetamide (33 ml) and pyridine (12.2 g) were added thereto, and the mixture was heated for refluxing for 30 minutes. 0.5 N hydrochloric acid (30 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate (120 ml). The extracted solution was washed with a sodium chloride aqueous solution (120 ml), then dried over magnesium sulfate, and concentrated. An oily product, ethyl p-(1-ethoxycarbonylpropanesulfonamido)benzoylacetate was quantitatively obtained. while cooling with ice the mixture was heated for refluxing for 30 minutes the mixture was extracted with ethyl acetate (120 ml) The extracted solution was washed with a sodium chloride aqueous solution (120 ml) dried over magnesium sulfate concentrated

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 440 ml of acetonitrile was dissolved 146 g of ethyl p-aminobenzoylacetate, and 70 ml of acetic anhydride was added dropwise to the solution at 40° C. After reacting at 40° C. for 1 hour, 48.8 g of 80% hydrazine hydrate was added thereto dropwise. After heat generation subsided, the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour. The reaction mixture was cooled to 5° C., and the precipitated crystals were filtered to yield 148 g of 3-(4-acetylaminophenyl)-2-pyrazolin-5-one as gray crystals having a melting point of 254° to 258° C. was added dropwise to the solution at 40° C After heat generation the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour the precipitated crystals were filtered

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a mixture comprising 224 g of reduced iron, 13.4 g of ammonium chloride, 1 liter of isopropyl alcohol and 0.2 liter of water was added 237 g of ethyl p-nitrobenzoylacetate in small portions at a temperature between 50° C. and 70° C. with caution against heat generation. The mixture was allowed to react at 70° C. for 1 hour, followed by filtration. To the filtrate was added 1 liter of water, and crystals precipitated upon cooling to 5° C. were separated by filtration to obtain 172 g of ethyl p-aminobenzoylacetate as yellow crystals having a melting point of 82° to 84° C. against heat generation to react at 70° C. for 1 hour followed by filtration To the filtrate was added 1 liter of water, and crystals precipitated were separated by filtration

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 440 ml of acetonitrile was dissolved 146 g of ethyl p-aminobenzoylacetate, and 70 ml of acetic anhydride was added dropwise to the solution at 40° C. After reacting at 40° C. for 1 hour, 48.8 g of 80% hydrazine hydrate was added thereto dropwise. After heat generation subsided, the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour. The reaction mixture was cooled to 5° C., and the precipitated crystals were filtered to yield 148 g of 3-(4-acetylaminophenyl)-2-pyrazolin-5-one as gray crystals having a melting point of 254° to 258° C. was added dropwise to the solution at 40° C After heat generation the reaction was further continued at a temperature between 55° C. and 60° C. for 1 hour the precipitated crystals were filtered

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Into a mixture comprising 224 g of reduced iron, 13.4 g of ammonium chloride, 1 liter of isopropyl alcohol and 0.2 liter of water was added 237 g of ethyl p-nitrobenzoylacetate in small portions at a temperature between 50° C. and 70° C. with caution against heat generation. The mixture was allowed to react at 70° C. for 1 hour, followed by filtration. To the filtrate was added 1 liter of water, and crystals precipitated upon cooling to 5° C. were separated by filtration to obtain 172 g of ethyl p-aminobenzoylacetate as yellow crystals having a melting point of 82° to 84° C. against heat generation to react at 70° C. for 1 hour followed by filtration To the filtrate was added 1 liter of water, and crystals precipitated were separated by filtration

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 224 g of reduced iron, 13.4 g of ammonium chloride, 1,000 ml of isopropyl alcohol, and 200 ml of water was prepared, and then 237 g of ethyl p-nitrobenzoylacetate was added thereto in small amounts at temperatures ranging between 50° and 70° C. They were reacted at 70° C. for 1 hour and then the reaction solution was filtered. Then, 1,000 ml of water was added to the filtrate and cooled to 5° C., and crystals precipitated were collected by filtration to yield 172 g of yellow ethyl p-aminobenzoylacetate crystals, m.p., 82°-4° C. was prepared ranging between 50° and 70° C They were reacted at 70° C. for 1 hour the reaction solution was filtered Then, 1,000 ml of water was added to the filtrate crystals precipitated were collected by filtration

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

Procedure: Ethanol (3.6 g) and tetrahydrofuran (10 ml) were dropwise added to a solution of 2-chlorosulfonylbutyl chloride (14.4 g) and tetrahydrofuran (21 ml) while cooling with ice. After stirring at room temperature for 1 hour, ethyl p-aminobenzoylacetate (13.3 g), N,N-dimethylacetamide (33 ml) and pyridine (12.2 g) were added thereto, and the mixture was heated for refluxing for 30 minutes. 0.5 N hydrochloric acid (30 ml) was added to the reaction solution, and the mixture was extracted with ethyl acetate (120 ml). The extracted solution was washed with a sodium chloride aqueous solution (120 ml), then dried over magnesium sulfate, and concentrated. An oily product, ethyl p-(1-ethoxycarbonylpropanesulfonamido)benzoylacetate was quantitatively obtained. while cooling with ice the mixture was heated for refluxing for 30 minutes the mixture was extracted with ethyl acetate (120 ml) The extracted solution was washed with a sodium chloride aqueous solution (120 ml) dried over magnesium sulfate concentrated