2-phenylisoindole-1,3-dione

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

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

Procedure: The reaction of aniline 3.8 g (0.041 mol) with phthalic anhydride 4.0 g (0.041) mol in 100 ml of refluxing glacial acetic acid for 3 hours, followed by precipitation from water, filtration and vacuum drying at 120° C., afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol). Lit. reports m.p. 210° C. ("Dict. Org. Cpds", 5, 2740(1965), Oxford Univ. Press, N.Y.). Anal. Calcd. for C14H9NO2 : C, 75.33; H, 4.06. Found: C, 75.10; H, 4.17%. Ir(KBr): 1765, 1700, and 1375 cm-1 (imide). followed by precipitation from water, filtration and vacuum drying at 120° C. afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol)

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

Procedure: A mixture of N-phenylphthalimide (100 g), zinc powder (147 g) and acetic acid (700 ml) is heated under reflux for 5.5 hours with stirring. After cooling, the mixture is filtered and the insoluble solid is washed with hot acetic acid (100 ml). The combined filtrate and washings are concentrated to give crystal (72 g, 78%). Recrystallization from benzene gives colorless scales. Melting point: 166° to 167° C. is heated under reflux for 5.5 hours After cooling the mixture is filtered the insoluble solid is washed with hot acetic acid (100 ml) The combined filtrate and washings are concentrated

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

Procedure: A mixture of N-phenylphthalimide (100 g), zinc powder (147 g) and acetic acid (700 ml) is heated under reflux for 5.5 hours with stirring. After cooling, the mixture is filtered and the insoluble solid is washed with hot acetic acid (100 ml). The combined filtrate and washings are concentrated to give crystal (72 g, 78%). Recrystallization from benzene gives colorless scales. Melting point: 166° to 167° C. is heated under reflux for 5.5 hours After cooling the mixture is filtered the insoluble solid is washed with hot acetic acid (100 ml) The combined filtrate and washings are concentrated

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

Procedure: A mixture of phthalic anhydride (19 g) and aniline (14 g) is heated at 140° to 145° C. for 50 minutes, and to the reaction mixture is added water (50 ml). The resulting powder is collected by filtration, washed with 10% aqueous potassium carbonate solution (50 ml) and water (100 ml), and dried to give colorless powder (28 g, 97%). Recrystallization from acetic acid gives colorless needles. is heated at 140° to 145° C. for 50 minutes The resulting powder is collected by filtration washed with 10% aqueous potassium carbonate solution (50 ml) and water (100 ml) dried

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

Procedure: A mixture of phthalic anhydride (19 g) and aniline (14 g) is heated at 140° to 145° C. for 50 minutes, and to the reaction mixture is added water (50 ml). The resulting powder is collected by filtration, washed with 10% aqueous potassium carbonate solution (50 ml) and water (100 ml), and dried to give colorless powder (28 g, 97%). Recrystallization from acetic acid gives colorless needles. is heated at 140° to 145° C. for 50 minutes The resulting powder is collected by filtration washed with 10% aqueous potassium carbonate solution (50 ml) and water (100 ml) dried

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

Procedure: Phenylphthalimidine of the formula (II) [L. Butula, D. Kolbah and I. Butula, Croat. Chem. Acta, 44 (4), 481, (1972),], which is a starting compound of the method of this invention, may be produced according to conventional methods. For example, Compound (II) is preferably produced in a high yield by heating aniline and phthalic anhydride in the absence of a solvent to give N-phenylphthalimide in an almost quantitative yield, and then subjecting the obtained N-phenylphthalimide to reduction with zinc and acetic acid. may be produced a high yield

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

Procedure: Phenylphthalimidine of the formula (II) [L. Butula, D. Kolbah and I. Butula, Croat. Chem. Acta, 44 (4), 481, (1972),], which is a starting compound of the method of this invention, may be produced according to conventional methods. For example, Compound (II) is preferably produced in a high yield by heating aniline and phthalic anhydride in the absence of a solvent to give N-phenylphthalimide in an almost quantitative yield, and then subjecting the obtained N-phenylphthalimide to reduction with zinc and acetic acid. may be produced a high yield

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

Procedure: 1.48 g of phthalic anhydride and 0.931 g of aniline were mixed under cooling with ice, and the mixture was reacted at a temperature of 180° C. for 2 hours. under cooling with ice the mixture was reacted at a temperature of 180° C. for 2 hours

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

Procedure: The reaction of aniline 3.8 g (0.041 mol) with phthalic anhydride 4.0 g (0.041) mol in 100 ml of refluxing glacial acetic acid for 3 hours, followed by precipitation from water, filtration and vacuum drying at 120° C., afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol). Lit. reports m.p. 210° C. ("Dict. Org. Cpds", 5, 2740(1965), Oxford Univ. Press, N.Y.). Anal. Calcd. for C14H9NO2 : C, 75.33; H, 4.06. Found: C, 75.10; H, 4.17%. Ir(KBr): 1765, 1700, and 1375 cm-1 (imide). followed by precipitation from water, filtration and vacuum drying at 120° C. afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol)

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

Procedure: The reaction of aniline 3.8 g (0.041 mol) with phthalic anhydride 4.0 g (0.041) mol in 100 ml of refluxing glacial acetic acid for 3 hours, followed by precipitation from water, filtration and vacuum drying at 120° C., afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol). Lit. reports m.p. 210° C. ("Dict. Org. Cpds", 5, 2740(1965), Oxford Univ. Press, N.Y.). Anal. Calcd. for C14H9NO2 : C, 75.33; H, 4.06. Found: C, 75.10; H, 4.17%. Ir(KBr): 1765, 1700, and 1375 cm-1 (imide). followed by precipitation from water, filtration and vacuum drying at 120° C. afforded an 8.2 g (91%) yield of product, m.p. 205°-9° C. (from ethanol)

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

Procedure: A mixture of N-phenylphthalimide (100 g), zinc powder (147 g) and acetic acid (700 ml) is heated under reflux for 5.5 hours with stirring. After cooling, the mixture is filtered and the insoluble solid is washed with hot acetic acid (100 ml). The combined filtrate and washings are concentrated to give crystal (72 g, 78%). Recrystallization from benzene gives colorless scales. Melting point: 166° to 167° C. is heated under reflux for 5.5 hours After cooling the mixture is filtered the insoluble solid is washed with hot acetic acid (100 ml) The combined filtrate and washings are concentrated