N-(3-chlorophenyl)acetamide

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: To fuming nitric acid (120 mL) at -50° C. was added N-acetyl-3-chloroaniline (30 g) over a period of 45 minutes. The reaction was kept between -50° C. and -30° C. using a dry ice/acetone bath. The reaction mixture was stirred for an additional hour and then poured into 1500 mL of crushed ice and water. The precipitate was filtered and slurried with 1 liter of slightly alkaline water (ammonium hydroxide) twice. The precipitate was then dried and recrystallized from toluene to yield (3.6 g) of N-acetyl-3-chloro-4-nitroaniline; m.p. 134°-136° C. was kept between -50° C. and -30° C. The precipitate was filtered The precipitate was then dried recrystallized from toluene

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 3-chloroaniline (10 g, 0.078 mol) was added portionwise acetic anhydride (32 g, 0.314 mol) in such a manner as to keep the temperature of the reaction mixture below 85° C. The reaction mixture was then stirred at 90° C. for 4 hours and then cooled to room temperature. The reaction mixture was then poured carefully into ice water, extracted with ethyl acetate and dried over sodium sulfate. The solvent was removed, yielding 30 g of N-acetyl-3-chloroaniline. the temperature of the reaction mixture below 85° C cooled to room temperature extracted with ethyl acetate dried over sodium sulfate The solvent was removed

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 775 ml of concentrated sulfuric acid, preheated to 70° C., was added, with stirring, 136 g of isonitroso-3-chloroacetanilide at such a rate as to maintain the reaction medium at a temperature between 75° and 85° C. When all the solid had been added, the reaction mixture was heated at 90° C. for an additional 30 minutes. The reaction mixture was then cooled, and poured slowly onto ca 2 liters of ice, with stirring. Additional ice was added as necessary to maintain the temperature below room temperature. A red-orange precipitate formed which was recovered by filtration, washed with water and dried. The resultant solid was slurried in 2 liters of water, and then it was brought into solution by the addition of ca 700 ml of 3 N sodium hydroxide. The solution was filtered, and then pH was adjusted to 8 with concentrated hydrochloric acid. At this point, 120 ml of a mixture of 80 parts water and 20 parts concentrated hydrochloric acid was added. The solid which precipitated was recovered by filtration, washed with water and dried to give 50 g of crude 4-chloroisatin. The filtrate from which the 4-chloroisatin had been recovered was further acidified to pH 0 using concentrated hydrochloric acid, whereupon a further precipitate formed. It was recovered by filtration, washed with water and dried, to give 43 g of crude 6-chloroisatin. preheated to 70° C. was added When all the solid had been added The reaction mixture was then cooled with stirring Additional ice was added as necessary to maintain the temperature below room temperature A red-orange precipitate formed which was recovered by filtration washed with water dried it was brought into solution by the addition of ca 700 ml of 3 N sodium hydroxide The solution was filtered At this point, 120 ml of a mixture of 80 parts water and 20 parts concentrated hydrochloric acid was added The solid which precipitated was recovered by filtration washed with water dried

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

Procedure: To a stirred solution of 113.23 g (0.686 mol) of chloral hydrate in 2 liters of water was added 419 g (2.95 mol) of sodium sulfate, followed by a solution prepared from 89.25 g (0.70 mol) of 3-chloroaniline, 62 ml of concentrated hydrochloric acid and 500 ml of water. A thick precipitate formed. To the reaction mixture was then added, with stirring, a solution of 155 g (2.23 mol) of hydroxylamine in 500 ml of water. Stirring was continued and the reaction mixture was warmed slowly and it was maintained between 60 and 75° C. for approximately 6 hours, during which time an additional 1 liter of water had been added to facilitate stirring. The reaction mixture was then cooled and the precipitate was recovered by filtration. The wet solid was dried to give 136.1 g of isonitroso-3-chloroacetanilide. A thick precipitate formed To the reaction mixture was then added Stirring the reaction mixture was warmed slowly had been added to facilitate stirring The reaction mixture was then cooled the precipitate was recovered by filtration The wet solid was dried

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

Procedure: To a stirred solution of 113.23 g (0.686 mol) of chloral hydrate in 2 liters of water was added 419 g (2.95 mol) of sodium sulfate, followed by a solution prepared from 89.25 g (0.70 mol) of 3-chloroaniline, 62 ml of concentrated hydrochloric acid and 500 ml of water. A thick precipitate formed. To the reaction mixture was then added, with stirring, a solution of 155 g (2.23 mol) of hydroxylamine in 500 ml of water. Stirring was continued and the reaction mixture was warmed slowly and it was maintained between 60 and 75° C. for approximately 6 hours, during which time an additional 1 liter of water had been added to facilitate stirring. The reaction mixture was then cooled and the precipitate was recovered by filtration. The wet solid was dried to give 136.1 g of isonitroso-3-chloroacetanilide. A thick precipitate formed To the reaction mixture was then added Stirring the reaction mixture was warmed slowly had been added to facilitate stirring The reaction mixture was then cooled the precipitate was recovered by filtration The wet solid was dried

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: A mixture of 1-bromo-4-methylaminoanthraquinone (16 parts) of the following formula: ##STR10## and m-chloroacetoanilide (12.7 parts) of the following formula: ##STR11## was heated at 135°-145° C. for 25 hours in o-dichlorobenzene in the presence of metallic copper (powder, 0.3 part) and potassium carbonate (17.3 parts). After cooling, the resulting precipitate was filtrated, washed with methanol and then water and dried to obtain a cake (13.5 parts, yield 70%) of anthrapyridone compound of the following formula: This compound showed a single red spot when thin-layer-chromatographed and λ max (in N,N-dimethylformamide) of 547 nm and had a melting point of 281°-284° C. (uncorrected). After cooling the resulting precipitate was filtrated washed with methanol water and dried

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 775 ml of concentrated sulfuric acid, preheated to 70° C., was added, with stirring, 136 g of isonitroso-3-chloroacetanilide at such a rate as to maintain the reaction medium at a temperature between 75° and 85° C. When all the solid had been added, the reaction mixture was heated at 90° C. for an additional 30 minutes. The reaction mixture was then cooled, and poured slowly onto ca 2 liters of ice, with stirring. Additional ice was added as necessary to maintain the temperature below room temperature. A red-orange precipitate formed which was recovered by filtration, washed with water and dried. The resultant solid was slurried in 2 liters of water, and then it was brought into solution by the addition of ca 700 ml of 3N sodium hydroxide. The solution was filtered, and then pH was adjusted to 8 with concentrated hydrochloric acid. At this point, 120 ml of a mixture of 80 parts water and 20 parts concentrated hydrochloric acid was added. The solid which precipitated was recovered by filtration, washed with water and dried to give 50 g of crude 4-chloroisatin. The filtrate from which the 4-chloroisatin had been recovered was further acidified to pH 0 using concentrated hydrochloric acid, wherenupon a further precipitate formed. It was recovered by filtration, washed with water and dried, to give 43 g of crude 6-chloroisatin. preheated to 70° C. was added When all the solid had been added The reaction mixture was then cooled with stirring Additional ice was added as necessary to maintain the temperature below room temperature A red-orange precipitate formed which was recovered by filtration washed with water dried it was brought into solution by the addition of ca 700 ml of 3N sodium hydroxide The solution was filtered At this point, 120 ml of a mixture of 80 parts water and 20 parts concentrated hydrochloric acid was added The solid which precipitated was recovered by filtration washed with water dried

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

Procedure: To a stirred solution of 113.23 g (0.686 mol) of chloral hydrate in 2 liters of water was added 419 g (2.95 mol) of sodium sulfate, followed by a solution prepared from 89.25 g (0.70 mol) of 3-chloroaniline, 62 ml of concentrated hydrochloric acid and 500 ml of water. A thick precipitate formed. To the reaction mixture was then added, with stirring, a solution of 155 g (2.23 mol) of hydroxylamine in 500 ml of water. Stirring was continued and the reaction mixture was warmed slowly and it was maintained between 60° and 75° C. for approximately 6 hours, during which time an additional 1 liter of water had been added to facilitate stirring. The reaction mixture was then cooled and the precipitate was recovered by filtration. The wet solid was dried to give 136.1 g of isonitroso-3-chloroacetanilide. A thick precipitate formed To the reaction mixture was then added Stirring the reaction mixture was warmed slowly had been added to facilitate stirring The reaction mixture was then cooled the precipitate was recovered by filtration The wet solid was dried