3-methyl-2,3-dihydroinden-1-one

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

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.5 g of 3-methyl-1-indanone, 1.37 g oxindole and 5 ml piperidine in 3 ml of dimethylforamide was heated in a sealed tube at 130° C. overnight to yield a reddish-brown suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 120 mg of 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid. to yield a reddish-brown suspension extracted with ethyl acetate The organic layer was washed with brine dried with magnesium sulfate concentrated

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.5 g of 3-methyl-1-indanone, 1.37 g oxindole and 5 ml piperidine in 3 ml of dimethylforamide was heated in a sealed tube at 130° C. overnight to yield a reddish-brown suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 120 mg of 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid. to yield a reddish-brown suspension extracted with ethyl acetate The organic layer was washed with brine dried with magnesium sulfate concentrated

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

Procedure: To 31.8 g of aluminum chloride, 6.8 g of crotonic acid and 50.0 ml of benzene were added and the mixture was reacted under reflux for 5 hours. After filtering the reaction solution, benzene was removed from the filtrate by distillation and the residue was distilled in a vacuum (120°-123° C./12 mmHg) to obtain 9.7 g of 3-methyl-1-indanone. the mixture was reacted under reflux for 5 hours After filtering the reaction solution, benzene was removed from the filtrate by distillation the residue was distilled in a vacuum (120°-123° C./12 mmHg)

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

Procedure: To 31.8 g of aluminum chloride, 6.8 g of crotonic acid and 50.0 ml of benzene were added and the mixture was reacted under reflux for 5 hours. After filtering the reaction solution, benzene was removed from the filtrate by distillation and the residue was distilled in a vacuum (120°-123° C./12 mmHg) to obtain 9.7 g of 3-methyl-1-indanone. the mixture was reacted under reflux for 5 hours After filtering the reaction solution, benzene was removed from the filtrate by distillation the residue was distilled in a vacuum (120°-123° C./12 mmHg)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: As presented in the following reaction formula, a solution of potassium nitrate (KNO2; 6.2 g, 0.06 mol) in sulfuric acid (30 mL) was added dropwise at 0° C. to a mixture of 3-methyl-2,3-dihydro-1H-inden-1-one (9.0 g, 0.06 mol) in sulfuric acid ic (H2SO4; 40 mL). Then, the mixture was stirred at 0° C. until the completion of reaction. The mixture obtained after the reaction was added to ice water and filtered. The cake was washed with water and purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.) using an eluent of pentane (PE):ethyl acetate (10:1 (by volume)) to give 3-methyl-6-nitro-2,3-dihydro-1-H-inden-1-one (8 g, yield: 69%) as a yellow solid. The mixture obtained after the reaction filtered The cake was washed with water purified by silica gel (100 g) column chromatography (product of Merck Co., Ltd.)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0° C., and the reaction mixture was stirred at 0° C. for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE):ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil. was refluxed under heating for 2 hours the thionyl chloride was removed by refluxing under heating After the completion of reaction extracted twice with 200 mL of dichloromethane (DCM) The combined organic phase was washed with water (100 mL) and saturated brine (100 mL) dried concentrated with magnesium sulfate to give a crude product The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.))

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: As presented in the following reaction formula, a mixture of 3-phenylbutanoic acid (30 g, 0.18 mol) in thionyl chloride (SOCl2; 100 mL) was refluxed under heating for 2 hours, and then the thionyl chloride was removed. Toluene (200 mL) and aluminum chloride (AlCl3; 24 g, 0.18 mol) were added to the resulting mixture at 0° C., and the reaction mixture was stirred at 0° C. for 0.5 hours, followed by refluxing under heating. After the completion of reaction, the mixture was treated with ice water and then extracted twice with 200 mL of dichloromethane (DCM). The combined organic phase was washed with water (100 mL) and saturated brine (100 mL), and dried and concentrated with magnesium sulfate to give a crude product. The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.)) using an eluent of pentane (PE):ethyl acetate (20:1 (by volume)) to give 3-methyl-2,3-dihydro-1H-inden-1-one (16 g, yield: 60%) as a brown oil. was refluxed under heating for 2 hours the thionyl chloride was removed by refluxing under heating After the completion of reaction extracted twice with 200 mL of dichloromethane (DCM) The combined organic phase was washed with water (100 mL) and saturated brine (100 mL) dried concentrated with magnesium sulfate to give a crude product The crude product was purified by gel column chromatography (using 100 g of silica gel (product of Merck Co., Ltd.))

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

Procedure: A solution of crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one. the mixture was refluxed for 7 hours Excess benzene was distilled off the reaction mixture was poured slowly into ice cold HCl The organic compound was extracted with ethylacetate The organic phase was washed thoroughly with water dried evaporated under vacuum The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm)

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

Procedure: A solution of crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one. the mixture was refluxed for 7 hours Excess benzene was distilled off the reaction mixture was poured slowly into ice cold HCl The organic compound was extracted with ethylacetate The organic phase was washed thoroughly with water dried evaporated under vacuum The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm)

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

Procedure: A solution of crotonic acid (20 g, 0.232 moles) in benzene (147 ml) was added AlCl3 (93 g, 0.748 moles) and the mixture was refluxed for 7 hours. Completion of the reaction was monitored by HPLC & GC. Excess benzene was distilled off and the reaction mixture was poured slowly into ice cold HCl. The organic compound was extracted with ethylacetate. The organic phase was washed thoroughly with water, dried, and evaporated under vacuum. The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm) giving 25 g (74%) of 99.2% pure 3-methyl-indan-1-one. the mixture was refluxed for 7 hours Excess benzene was distilled off the reaction mixture was poured slowly into ice cold HCl The organic compound was extracted with ethylacetate The organic phase was washed thoroughly with water dried evaporated under vacuum The resultant oil was purified by high vacuum distillation (90-94° C. at ˜2 mm)

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 0.5 g of 3-methyl-1-indanone, 1.37 g oxindole and 5 ml piperidine in 3 ml of dimethylforamide was heated in a sealed tube at 130° C. overnight to yield a reddish-brown suspension. The mixture was added to 1N hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried with magnesium sulfate and concentrated. Chromatography afforded 120 mg of 3-(3-methylindan-1-ylidene)-1,3-dihydroindol-2-one as an orange solid. to yield a reddish-brown suspension extracted with ethyl acetate The organic layer was washed with brine dried with magnesium sulfate concentrated