1,3-diphenylpropan-2-one

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: It is known to produce pyridines having aromatic substituents in the 2- and 3-positions from ketones, namely, 2,3-diphenyl pyridine from desoxybenzoin and 2-benzyl-3-phenyl pyridine from 1,3-diphenylacetone. The ketone for this purpose is first converted to the enamine, this reacted with 3-bromo-propylamine hydrobromide in dimethyl formamide to the tetrahydropyridines and these finally dehydrogenated in the presence of palladium catalyst to the pyridines (Org. Chem. Vol. 28 (1963) pages 3468 to 3473). In the case of the production of 2,3-diphenyl pyridine from desoxybenzoin this can also be reacted with 3,3-diethoxy-1-dimethylamino-1-propene to form 5-dimethylamino-1,2-diphenyl-2,4-pentadien-1-one and this reacted with triethyloxonium tetrafluoroborate and further with dimethylamine to 5-dimethylamino-N,N-dimethyl-1,2-diphenyl-2,4-pentadieniminium-tetrafluoroborate and finally this converted into the 2,3-diphenyl pyridine by heating in an ammonium chloride-ammonia solution (Liebigs Ann. Chem. 1975 pages 874 to 900).

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: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water

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

Procedure: A 1.4 g. portion of 1,3-diphenyl-2-propanone was mixed with 1.0 g. of tris(formylamino)methane in 20 ml. of dimethylformamide. The reaction mixture was stirred at reflux temperature for 3 hours. The mixture was then cooled to approximately room temperature, and poured into water. The precipitated solids were separated by filtration, and the solids were suspended in chloroform. The chloroform was then filtered, and the solids remaining were washed first with water, and then with chloroform. The yield was about 100 mg. of 3,5-diphenyl-4(1H)-pyridone, m.p. greater than 335° C. at reflux temperature for 3 hours The mixture was then cooled to approximately room temperature The precipitated solids were separated by filtration The chloroform was then filtered the solids remaining were washed first with water

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

Procedure: The compounds of this invention can be prepared by various synthetic routes. Benary and Bitter, Ber. 61, 1058 (1928) taught the synthesis of an intermediate disodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one by the condensation of 1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium methoxide. The intermediate pentadienone is neutralized by strong acid and forms 3,5-diphenyl-4-pyrone. Reaction of the pyrone with ammonium acetate at an elevated temperature produces 3,5-diphenyl-4(1H)-pyridone. The compounds of this invention can be prepared by various synthetic routes

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

Procedure: The compounds of this invention can be prepared by various synthetic routes. Benary and Bitter, Ber. 61, 1058 (1928) taught the synthesis of an intermediate disodium salt of 1,5-dihydroxy-2,4-diphenyl-1,4-pentadien-3-one by the condensation of 1,3-diphenyl-2-propanone with ethyl formate in the presence of sodium methoxide. The intermediate pentadienone is neutralized by strong acid and forms 3,5-diphenyl-4-pyrone. Reaction of the pyrone with ammonium acetate at an elevated temperature produces 3,5-diphenyl-4(1H)-pyridone. The compounds of this invention can be prepared by various synthetic routes

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-Diphenylacetone (17.5 g, 83 mMole) was dissolved in methanol (240 mL) and heated to 65° C. To the solution was added 5-bromoacenaphthenequinone (2), (20 g, 75 mMole). The resulting well-stirred suspension was then treated with 1M-methanolic KOH (100 ML, 100 mMole) at a fast drip rate, whereupon the dark colored product precipitated immediately. The mixture was then stirred at 65° C. for 1 hour, cooled and filtered. The black solid was washed well with methanol, ether and dried. Yield of product (3), (31 g). precipitated immediately The mixture was then stirred at 65° C. for 1 hour cooled filtered The black solid was washed well with methanol, ether dried

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,3-Diphenylacetone (17.5 g, 83 mMole) was dissolved in methanol (240 mL) and heated to 65° C. To the solution was added 5-bromoacenaphthenequinone (2), (20 g, 75 mMole). The resulting well-stirred suspension was then treated with 1M-methanolic KOH (100 ML, 100 mMole) at a fast drip rate, whereupon the dark colored product precipitated immediately. The mixture was then stirred at 65° C. for 1 hour, cooled and filtered. The black solid was washed well with methanol, ether and dried. Yield of product (3), (31 g). precipitated immediately The mixture was then stirred at 65° C. for 1 hour cooled filtered The black solid was washed well with methanol, ether dried