7-methyl-1H-indole-2,3-dione

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

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

Procedure: To a suspension of 4.91 g of 7-methylisatin in 100 ml of ethanol was added a solution of 5.59 g of O-benzylhydroxylamine hydrochloride and 3.29 g of sodium acetate in 40 ml of water at room temperature. The mixture was stirred at room temperature for 3 hours and concentrated. The concentrate was diluted with chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated. Recrystallization of the crude product from benzene yielded 5.40 g (68%) of the title compound. concentrated The concentrate was diluted with chloroform washed with water The organic layer was dried over anhydrous sodium sulfate concentrated Recrystallization of the crude product from benzene

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

Procedure: The 7-methylisatin (16.1 g, 0.1 mole) is suspended in dichloroethane (2000 ml) and the suspension is heated and irradiated with a high intensity light source to the reflux point. Bromine (24.3 g, 0.15 mole) is added dropwise over a one hour period. the suspension is heated irradiated with a high intensity light source to the reflux point

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 5 l flask is placed chloral hydrate (90 g, 0.54 mole) and water (1200 ml). To this solution is added sodium sulfate decahydrate (1300 g, 10.9 mole) followed by a solution of o-methylaniline (54 g, 0.5 mole) in water (300 ml) containing concentrated hydrochloric acid (43 ml, 0.5 mole). Then a solution of hydroxylamine hydrochloride (110 g, 1.58 mole) in water (50 ml) is added. The reaction mixture is heated to reflux over a 90 minute period and refluxed 30 minutes. The reaction is cooled in ice and the resulting crystalline ortho-isonitrosoacetotoluidide is isolated by filtration and air dried. The orthoisonitrosoacetotoluidide is dissolved in portions in concentrated sulfuric acid (325 ml) that is preheated to 50° C. with vigorous stirring. The reaction temperature is maintained under 75° C. When the addition is complete, the mixture is heated at 80° C. for 30 minutes, cooled, and poured unto ice (3 kg). The 7-methylisatin is isolated by filtration. The 7-methylisatin is purified by dissolution in dilute sodium hydroxide. The basic solution is treated with 4N hydrochloric acid until a slight amount of precipitation is evident. The mixture is filtered and the filtrate is acidified. The pure 7-methylisatin is recovered by filtration and dried in vacuo at 80° C. and 0.1 mm pressure, mp 114°-145° C. (A. Wahl, et al., Ann. Chim. 5 314 (1926). In a 5 l flask is placed The reaction mixture is heated to reflux over a 90 minute period refluxed 30 minutes The reaction is cooled in ice the resulting crystalline ortho-isonitrosoacetotoluidide is isolated by filtration and air dried The orthoisonitrosoacetotoluidide is dissolved in portions in concentrated sulfuric acid (325 ml) that is preheated to 50° C. with vigorous stirring When the addition the mixture is heated at 80° C. for 30 minutes cooled poured unto ice (3 kg)

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

Procedure: To a suspension of 4.91 g of 7-methylisatin in 100 ml of ethanol was added a solution of 5.59 g of O-benzylhydroxylamine hydrochloride and 3.29 g of sodium acetate in 40 ml of water at room temperature. The mixture was stirred at room temperature for 3 hours and concentrated. The concentrate was diluted with chloroform and washed with water. The organic layer was dried over anhydrous sodium sulfate and concentrated. Recrystallization of the crude product from benzene yielded 5.40 g (68%) of the title compound. concentrated The concentrate was diluted with chloroform washed with water The organic layer was dried over anhydrous sodium sulfate concentrated Recrystallization of the crude product from benzene

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

Procedure: A suspension of 16.1 g of 7-methyl-2,3-indolinedione in 120 ml of water was treated with a sufficient amount of a solution of 16.6 of sodium hydroxide in 55 ml of water to provide solution. A warm solution of 25.4 g of acetoxyacetylbiphenyl in 350 ml of ethanol was added, followed by the balance of the alkali solution. The mixture was refluxed for 2.5 hours. During the last 1/2 hour 50 ml of ethanol was distilled off. A 300 ml portion of water was added, the mixture was stirred, cooled and filtered through diatomaceous earth. The filtrate was treated with 34 ml of concentrated hydrochloric acid and 12 ml of glacial acetic acid. The resulting solid was collected and recrystallized from ethanol/water, giving 13.6 g of the desired product, mp 178°-180° C. to provide solution The mixture was refluxed for 2.5 hours During the last 1/2 hour 50 ml of ethanol was distilled off A 300 ml portion of water was added cooled filtered through diatomaceous earth The filtrate was treated with 34 ml of concentrated hydrochloric acid and 12 ml of glacial acetic acid The resulting solid was collected recrystallized from ethanol/water

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

Procedure: 15 parts of 50 percent strength by weight hydrogen peroxide solution are added slowly to a solution of 32.2 parts of 7-methylisatin and 12 parts of sodium methylate in 400 parts of methanol at 0° C. Thereafter, the mixture is stirred for 2 hours at room temperature and worked up as described in Example 1. 25.5 parts (78% of theory) of methyl 3-methylanthranilate, of melting point 27°-29° C., are obtained.

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

Procedure: 38.2 g of pure phenol were mixed with 0.4 g of concentrated sulphuric acid, with stirring and heating to 60° C. 28.5 g (0.177 mole) of 7-methylisatin were added in portions. At the end of the addition, the temperature was raised to 85° C. and 21 g of PhOAc were gradually added dropwise over a period of 5 hours. Finally, the temperature of the stirred mixture was raised to 120° C. for 30 minutes. It was then allowed to cool, filtered and washed with abundant water to remove the PhOAc. The resulting solid was dried and gave 50 g. It was dissolved in acetone and precipitated with chloroform, allowed to cool and filtered. The solid formed was dried to yield 30 g of 3,3-bis-(4-hydroxyphenyl)-7-methyl-2 -indolinone, m.p. 272°-4° C. Yield: 52%. At the end of the addition the temperature was raised to 85° C. Finally, the temperature of the stirred mixture was raised to 120° C. for 30 minutes to cool filtered washed with abundant water to remove the PhOAc The resulting solid was dried gave 50 g precipitated with chloroform to cool filtered The solid formed was dried

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

Procedure: 32.2 parts of 7-methylisatin are introduced into a solution of 56 parts of potassium peroxydisulfate in 450 parts of 92% strength sulfuric acid at from 0° C. to 10° C. The mixture is then stirred for a few minutes, after which it is poured onto ice. The product is filtered off and dried, giving 31.4 parts of 5-methyl-2,3-dioxo-1,4-benzoxazine, of melting point 247°-249° C. after which it is poured onto ice The product is filtered off dried

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

Procedure: 32.2 parts of 7-methylisatin are introduced into a solution of 56 parts of potassium peroxydisulfate in 450 parts of 92% strength sulfuric acid at from 0° C. to 10° C. The mixture is then stirred for a few minutes, after which it is poured onto ice. The product is filtered off and dried, giving 31.4 parts of 5-methyl-2,3-dioxo-1,4-benzoxazine, of melting point 247°-249° C. after which it is poured onto ice The product is filtered off dried

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

Procedure: The 7-methylisatin (16.1 g, 0.1 mole) is suspended in dichloroethane (2000 ml) and the suspension is heated and irradiated with a high intensity light source to the reflux point. Bromine (24.3 g, 0.15 mole) is added dropwise over a one hour period. the suspension is heated irradiated with a high intensity light source to the reflux point

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

Procedure: The 7-methylisatin (16.1 g, 0.1 mole) is suspended in dichloroethane (2000 ml) and the suspension is heated and irradiated with a high intensity light source to the reflux point. Bromine (24.3 g, 0.15 mole) is added dropwise over a one hour period. the suspension is heated irradiated with a high intensity light source to the reflux point