2-(1H-indol-2-yl)phenol

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

Procedure: 11.26 g of 4-dimethylaminobenzophenone and 10.5 g of 2-(2'-hydroxyphenyl)-indole are stirred in 50 ml of phosphorus oxychloride for 4 hours under reflux. The reaction mixture is poured onto ice and rendered alkaline with ammonia and the resulting precipitate is then filtered off. Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid and precipitating with ammonia and water gives a slightly impure product, which is purified through a column, packed with 80 g of silica gel/ethyl acetate. Crystallisation from ethyl acetate/ethanol gives 16.7 g of 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole of the formula ##STR17## in the form of yellowish crystals with a melting point of 229°-231° C. On silton clay, this colour-forming agent develops a blue colour with a λ max of 600 nm. under reflux The reaction mixture is poured onto ice the resulting precipitate is then filtered off Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid precipitating with ammonia and water gives a slightly impure product, which is purified through a column Crystallisation from ethyl acetate/ethanol

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

Procedure: 7.7 g of 4,4'-bisdimethylaminobenzophenone was dissolved in 50 ml of chloroform, and the solution was stirred. Phosphorus oxychloride (5 g) and 10 ml of chloroform were added thereto, and the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.). Then, 6 g of 2-(2'-hydroxyphenyl)indole was added thereto, and the mixture was stirred at room temperature for 3 hours. The mixture was heated under reflux for an additional 2 hours. The heated mixture was cooled to room temperature, and poured into ice water, and neutralized with an aqueous solution of sodium hydroxide. Furthermore, 200 to 300 ml of chloroform was added for extraction. The chloroform layer was washed with water, dried, and distilled under reduced pressure to remove the chloroform. The remaining oily substance was dissolved in a small amount of methanol by heating, and the solution was cooled. The crystals precipitated were separated by filtration, and dried to obtain 4 g of the objective compound having a melting point of 165° to 168° C. the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.) the mixture was stirred at room temperature for 3 hours The mixture was heated under reflux for an additional 2 hours The chloroform layer was washed with water dried distilled under reduced pressure to remove the chloroform The remaining oily substance was dissolved in a small amount of methanol by heating the solution was cooled The crystals precipitated were separated by filtration dried

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

Procedure: 11.26 g of 4-dimethylaminobenzophenone and 10.5 g of 2-(2'-hydroxyphenyl)-indole are stirred in 50 ml of phosphorus oxychloride for 4 hours under reflux. The reaction mixture is poured onto ice and rendered alkaline with ammonia and the resulting precipitate is then filtered off. Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid and precipitating with ammonia and water gives a slightly impure product, which is purified through a column, packed with 80 g of silica gel/ethyl acetate. Crystallisation from ethyl acetate/ethanol gives 16.7 g of 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole of the formula ##STR17## in the form of yellowish crystals with a melting point of 229°-231° C. On silton clay, this colour-forming agent develops a blue colour with a λ max of 600 nm. under reflux The reaction mixture is poured onto ice the resulting precipitate is then filtered off Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid precipitating with ammonia and water gives a slightly impure product, which is purified through a column Crystallisation from ethyl acetate/ethanol

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

Procedure: 7.7 g of 4,4'-bisdimethylaminobenzophenone was dissolved in 50 ml of chloroform, and the solution was stirred. Phosphorus oxychloride (5 g) and 10 ml of chloroform were added thereto, and the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.). Then, 6 g of 2-(2'-hydroxyphenyl)indole was added thereto, and the mixture was stirred at room temperature for 3 hours. The mixture was heated under reflux for an additional 2 hours. The heated mixture was cooled to room temperature, and poured into ice water, and neutralized with an aqueous solution of sodium hydroxide. Furthermore, 200 to 300 ml of chloroform was added for extraction. The chloroform layer was washed with water, dried, and distilled under reduced pressure to remove the chloroform. The remaining oily substance was dissolved in a small amount of methanol by heating, and the solution was cooled. The crystals precipitated were separated by filtration, and dried to obtain 4 g of the objective compound having a melting point of 165° to 168° C. the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.) the mixture was stirred at room temperature for 3 hours The mixture was heated under reflux for an additional 2 hours The chloroform layer was washed with water dried distilled under reduced pressure to remove the chloroform The remaining oily substance was dissolved in a small amount of methanol by heating the solution was cooled The crystals precipitated were separated by filtration dried

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

Procedure: 11.26 g of 4-dimethylaminobenzophenone and 10.5 g of 2-(2'-hydroxyphenyl)-indole are stirred in 50 ml of phosphorus oxychloride for 4 hours under reflux. The reaction mixture is poured onto ice and rendered alkaline with ammonia and the resulting precipitate is then filtered off. Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid and precipitating with ammonia and water gives a slightly impure product, which is purified through a column, packed with 80 g of silica gel/ethyl acetate. Crystallisation from ethyl acetate/ethanol gives 16.7 g of 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole of the formula ##STR17## in the form of yellowish crystals with a melting point of 229°-231° C. On silton clay, this colour-forming agent develops a blue colour with a λ max of 600 nm. under reflux The reaction mixture is poured onto ice the resulting precipitate is then filtered off Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid precipitating with ammonia and water gives a slightly impure product, which is purified through a column Crystallisation from ethyl acetate/ethanol

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

Procedure: 7.7 g of 4,4'-bisdimethylaminobenzophenone was dissolved in 50 ml of chloroform, and the solution was stirred. Phosphorus oxychloride (5 g) and 10 ml of chloroform were added thereto, and the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.). Then, 6 g of 2-(2'-hydroxyphenyl)indole was added thereto, and the mixture was stirred at room temperature for 3 hours. The mixture was heated under reflux for an additional 2 hours. The heated mixture was cooled to room temperature, and poured into ice water, and neutralized with an aqueous solution of sodium hydroxide. Furthermore, 200 to 300 ml of chloroform was added for extraction. The chloroform layer was washed with water, dried, and distilled under reduced pressure to remove the chloroform. The remaining oily substance was dissolved in a small amount of methanol by heating, and the solution was cooled. The crystals precipitated were separated by filtration, and dried to obtain 4 g of the objective compound having a melting point of 165° to 168° C. the mixture was stirred for 30 minutes at room temperature (about 20°-30° C.) the mixture was stirred at room temperature for 3 hours The mixture was heated under reflux for an additional 2 hours The chloroform layer was washed with water dried distilled under reduced pressure to remove the chloroform The remaining oily substance was dissolved in a small amount of methanol by heating the solution was cooled The crystals precipitated were separated by filtration dried

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

Procedure: 11.26 g of 4-dimethylaminobenzophenone and 10.5 g of 2-(2'-hydroxypenyl)-indole are stirred in 50 ml of phosphorus oxychloride for 4 hours under reflux. The reaction mixture is poured onto ice and rendered alkaline with ammonia and the resulting precipitate is then filtered off. Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid and precipitating with ammonia and water gives a slightly impure product, which is purified through a column, packed with 80 g of silica gel/ethyl acetate. Crystallisation from ethyl acetate/ethanol gives 16.7 g of 6-phenyl-6-(4-dimethylaminophenyl)-6H-chromeno[4,3-b]-indole of the formula ##STR17## in the form of yellowish crystals with a melting point of 229°-2 31° C. On silton clay, this colour-forming agent develops a blue colour with a λ max of 600 nm. under reflux The reaction mixture is poured onto ice the resulting precipitate is then filtered off Repeated dissolving of the residue in methanol with the addition of a little 37% strength hydrochloric acid precipitating with ammonia and water gives a slightly impure product, which is purified through a column Crystallisation from ethyl acetate/ethanol