3-phenylfuran-2,5-dione

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

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: 4.0 g (23 mmole) of 3-phenylfuran-2,5-dione was added to a 100 ml single-necked round bottom flask followed by 2.9 g (27.6 mmole) of hydrazine monohydrate and then 20 ml of reagent grade ethanol (95%). The flask was fitted with a reflux condenser and the reaction mixture was heated to reflux in an oil bath at 110 degree (temperature of oil bath) and stirred for 2 h. The flask was then removed from the oil bath and the reaction mixture cooled to ambient temperature. The stir bar was removed and the solvent was evaporated in vacuo in a water bath at 45 degree. The residue was then treated with 50 ml of Milli-Q water and stirred for 10 minutes to give a suspension. The precipitate was collected by filtering, washed with 100 ml of Milli-Q water, and dried over a medium frit sintered glass funnel in vacuo to give 3.9 g of white solid. Yield, 91%, confirmed by ESI-MS. ESI-MS: m/z 189.2 (M+H). The flask was fitted with a reflux condenser the reaction mixture was heated to reflux in an oil bath at 110 degree (temperature of oil bath) The flask was then removed from the oil bath The stir bar was removed the solvent was evaporated in vacuo in a water bath at 45 degree The residue was then treated with 50 ml of Milli-Q water stirred for 10 minutes to give a suspension The precipitate was collected by filtering washed with 100 ml of Milli-Q water dried over a medium frit sintered glass funnel in vacuo

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

Procedure: Phenylmaleic anhydride (20 g, 115 mmol), sodium acetate trihydrate (1875 g, 138 mmol), hydrazine monohydrate (6.68 ml, 133 mmol) and 40% aqueous acetic acid (400 ml) were heated at reflux for 15 h then allowed to cool. The reaction mixture was left to cool in the fridge for 1 h. The solid produced was filtered and washed with water and diethyl ether before drying in a vacuum oven at 40° C. to give the required product (7.26 g). 1H NMR (250 MHz, DMSO) δ 3.43 (2H, broad peak), 7.17 (1H, s), 7.44 (3H, m), 7.81 (2H, m); MS (ES+) m/e 189 [MH+]. at reflux for 15 h to cool The reaction mixture was left to cool in the fridge for 1 h The solid produced was filtered washed with water and diethyl ether before drying in a vacuum oven at 40° C.

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

Procedure: Following the general procedure of Example I, 150 mmols of maleic anhydride were reacted with 25 mmols of distilled aniline in 60 mL of acetonitrile and in the presence of 38 mmols of concentrated HCl and 2.5 mmols of cuprous oxide. The process resulted in a 29.2% yield of 3-phenylmaleic anhydride.

Conditions: temp:7.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylmaleic anhydride (30 g, 0.17 mol), sodium acetate trihydrate (28 g, 0.21 mol) and hydrazine monohydrate (10 ml, 0.21 mol) were heated together at reflux in 40% acetic acid (600 ml) for 18 h. The mixture was cooled at 7° C. for 2 h, then filtered. The solid was washed with diethyl ether and dried in vacuo to give 11 g (34%) of the title compound: 1H NMR (250 MHz, DMSO-d6) δ 7.16 (1H, br s), 7.44 (5H, m), 7.80 (2H, br s); MS (ES+) m/e 189 [MH+]. filtered The solid was washed with diethyl ether dried in vacuo

Conditions: temp:7.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Phenylmaleic anhydride (30 g, 0.17 mol), sodium acetate trihydrate (28 g, 0.21 mol) and hydrazine monohydrate (10 ml, 0.21 mol) were heated together at reflux in 40% acetic acid (600 ml) for 18 h. The mixture was cooled at 7° C. for 2 h, then filtered. The solid was washed with diethyl ether and dried in vacuo to give 11 g (34%) of the title compound: 1H NMR (250 MHz, DMSO-d6) δ 7.16 (1H, br s), 7.44 (5H, m), 7.80 (2H, br s); MS (ES+) m/e 189 [MH+]. filtered The solid was washed with diethyl ether dried in vacuo

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 g (264.1 mmol) 3-Phenyl-furan-2,5-dione were suspended in 1.56 L water. After addition of 34.4 g (264.1 mmol) hydrazine sulfate the reaction mixture was heated to reflux (bath temperature: 115° C.) and kept there for five hours. During the night the reaction mixture was kept at a bath temperature of 98° C. After cooling the precipitate was sucked off, washed with water (100 mL) and dried at 40° C. yielding 47.6 g (95.8%) of the title compound. was heated During the night the reaction mixture was kept at a bath temperature of 98° C After cooling the precipitate washed with water (100 mL) dried at 40° C.

Conditions: temp:115.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 46 g (264.1 mmol) 3-Phenyl-furan-2,5-dione were suspended in 1.56 L water. After addition of 34.4 g (264.1 mmol) hydrazine sulfate the reaction mixture was heated to reflux (bath temperature: 115° C.) and kept there for five hours. During the night the reaction mixture was kept at a bath temperature of 98° C. After cooling the precipitate was sucked off, washed with water (100 mL) and dried at 40° C. yielding 47.6 g (95.8%) of the title compound. was heated During the night the reaction mixture was kept at a bath temperature of 98° C After cooling the precipitate washed with water (100 mL) dried at 40° C.

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

Procedure: In a manner analogous to that described in Example 3(A), from 0.7 g of (aminomethyl)[(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl]phosphinic acid methyl ester acetate and 0.29 g of phenylmaleic anhydride, there was obtained 0.21 g of [(RS)-4-methyl-2-[[(S)-3-methyl-1-(methylcarbamoyl)butyl]carbamoyl]pentyl][(2-phenylmaleimido)methyl]phosphinic acid methyl ester in the form of a pale yellow foam.

Conditions: temp:220.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the same autoclave as used in Example 1, 50 ml of benzene, 0.98 g of maleic anhydride and 0.019 g of Rh4 (CO)12 were charged, followed by supply of carbon monoxide under 30 kg/cm2. The charge in the autoclave was heated at 220° C. for 7 hours. The reaction mixture was cooled and benzene was removed by distillation under reduced pressure. The residue was separated by silica column chromatography to obtain 0.363 g of phenylmaleic anhydride and 0.136 g of succinic anhydride. Each product was identified based on the infrared absorption spectrum (hereinafter referred to as "IR") of the standard substance and the retention time in GC. were charged The charge in the autoclave The reaction mixture was cooled benzene was removed by distillation under reduced pressure The residue was separated by silica column chromatography