4-(diethylamino)benzaldehyde

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

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2-Picoline (9.3 g, 0.1 mole) and benzyl bromide (17.1 g, 0.1 mole) were refluxed in isopropanol (50 ml) overnight. The solvent was evaporated giving an oil which was heated at 100° C. for six hours. The resulting crude oil (8.5 g, 0.032 mole) and 4-diethylaminobenzaldehyde (6.0 g, 0.033 mole) were refluxed in methanol (40 ml) in the presence of piperidine (0.2 ml) under nitrogen for three hours. On cooling dark-coloured crystals were obtained which were collected to give 1-benzyl-2-[4-(diethylamino)styryl]pyridinium bromide (6.2 g), melting point 231°-233° C. The solvent was evaporated giving an oil which On cooling dark-coloured crystals were obtained which were collected

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

Procedure: 1-Dodecyl-2-methylpyridinium bromide (3.42 g), 0.01 mole) and 4-diethylaminobenzaldehyde (1.9 g), 0.011 mole) were refluxed in ethanol (15 ml) in the presence of piperidine (0.2 ml) under nitrogen for two hours. The solution was cooled and ether was added when an orange solid crystallised which was collected giving 2-[4-(diethylamino)styryl]-1-dodecylpyridinium bromide hemihydrate, (2.1 g), melting point 199°-200° C. The solution was cooled crystallised which was collected

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

Procedure: 1-Hexyl-2-methylpyridinium bromide (7.8 g, 0.03 mole) and 4-diethylaminobenzaldehyde (7.0 g, 0.04 mole) were refluxed in methanol (50 ml) in the presence of piperidine (1.0 ml) under nitrogen for four hours. The solution was evaporated and the resulting oil was redissolved in a small amount of isopropanol. Addition of twice the volume of ether gave a red crystalline solid which was collected and washed with isopropanol/ether to give 2-[4-(diethylamino)styryl]-1-hexylpyridinium bromide hemihydrate (5.8 g), melting point 222°-223° (decomposition). The solution was evaporated the resulting oil was redissolved in a small amount of isopropanol Addition of twice the volume of ether gave a red crystalline solid which was collected washed with isopropanol/ether

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

Procedure: 5-Ethyl-2-methyl-1-propylpyridinium bromide (7.32 g, 0.03 mole) and 4-diethylaminobenzaldehyde (7.0 g, 0.04 mole) were refluxed for four hours in methanol (50 ml) in the presence of piperidine (1 ml) under nitrogen. On cooling and addition of ether no precipitate was obtained. The solution was evaporated to give a red oil which was dissolved in isopropanol and twice the volume of ether was added, when a red crystalline solid was obtained (5.4 g). 2 Grams were re-dissolved in isopropanol and isopropyl ether was added to give red crystals of 2-[4-(diethylamino)styryl]-5-ethyl-1-propylpyridinium bromide hemihydrate (1.6 g), melting point 165°-167° (decomposition). On cooling was obtained The solution was evaporated to give a red oil which when a red crystalline solid was obtained (5.4 g)

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 18 g of 50% by weight sodium hydroxide solution were added dropwise to 17.7 g of p-diethylaminobenzaldehyde and 26.4 g of acetophenone in 150 ml of ethanol at 20° C. The mixture was then stirred at 20° C. for 2 hours and at 50° C. for 5 hours. The precipitate was filtered off and washed with ethanol until the residue was only pale yellowish and then with water until neutral. 33.6 g of 3-(p-diethylaminophenyl) -1,5-diphenylpentane-1,5-dione were obtained. The almost colorless crystals melt at 110° C. The precipitate was filtered off washed with ethanol until the residue

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

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 30 ml of dimethylformamide were dissolved 3.82 g of 3-carboxymethylrhodanine and 3.54 g of p-diethylaminobenzaldehyde, and the solution was stirred at 100° C. for 3 hours. After termination of the reaction, the solution was poured into water, and the formed precipitate was recovered by filtration, washed with water and recrystallized from acetone to obtain 3-carboxymethyl-5-(p-diethylaminobenzylidene)rhodanine (the yield was 87%). After termination of the reaction the formed precipitate was recovered by filtration washed with water recrystallized from acetone

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 30 ml of dimethylformamide were dissolved 3.82 g of 3-carboxymethylrhodanine and 3.54 g of p-diethylaminobenzaldehyde, and the solution was stirred at 100° C. for 3 hours. After termination of the reaction, the solution was poured into water, and the formed precipitate was recovered by filtration, washed with water and recrystallized from acetone to obtain 3-carboxymethyl-5-(p-diethylaminobenzylidene)rhodanine (the yield was 87%). After termination of the reaction the formed precipitate was recovered by filtration washed with water recrystallized from acetone

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

Procedure: 122.2 g (731 mmols) of p-nitrobenzoic acid, 11.3 g of dimethylsulfoxide, 2.0 g of a 5% platinum-supported catalyst, and 260 g of methanol were charged into a one liter autoclave, followed by filling hydrogen at a pressure of about 4 kg/cm2 and continuing agitation at room temperature until an equivalent of hydrogen was reacted with p-nitrobenzoic acid. After removal of the catalyst, 120.0 g (677 mmols) of 4-diethylaminobenzaldehyde, 30.0 g of acetic acid and 100 g of methanol were added to the resultant residue, followed by agitation at room temperature for 5 hours. After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals and dried to isolate 187.6 g (yield 88.7%) of α-p-(diethylamino)phenyl]-N-(4-carboxyphenyl)nitrone with a purity of 96%. The thus obtained α-[p-(diethylamino)-phenyl]-N-(4-carboxyphenyl)nitrone had the following results with respect to mass spectra (MS), NMR spectra (NMR), IR spectra (IR) and elementary analysis. were charged into a one liter autoclave at room temperature After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals dried

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

Procedure: 122.2 g (731 mmols) of p-nitrobenzoic acid, 11.3 g of dimethylsulfoxide, 2.0 g of a 5% platinum-supported catalyst, and 260 g of methanol were charged into a one liter autoclave, followed by filling hydrogen at a pressure of about 4 kg/cm2 and continuing agitation at room temperature until an equivalent of hydrogen was reacted with p-nitrobenzoic acid. After removal of the catalyst, 120.0 g (677 mmols) of 4-diethylaminobenzaldehyde, 30.0 g of acetic acid and 100 g of methanol were added to the resultant residue, followed by agitation at room temperature for 5 hours. After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals and dried to isolate 187.6 g (yield 88.7%) of α-p-(diethylamino)phenyl]-N-(4-carboxyphenyl)nitrone with a purity of 96%. The thus obtained α-[p-(diethylamino)-phenyl]-N-(4-carboxyphenyl)nitrone had the following results with respect to mass spectra (MS), NMR spectra (NMR), IR spectra (IR) and elementary analysis. were charged into a one liter autoclave at room temperature After removal of the resultant crystals by filtration, they were washed with methanol to obtain yellow crystals dried