naphthalene-1,8-diamine

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

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

Procedure: Dissolve 1-Benzyl-4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine (263.3 mg, 1.00 equiv; 0.662 mmoles) and 1,8-Naphthalenediamine, N,N,N′,N′-Tetramethyl-(0.05 equiv, 0.033 mmoles, 7.0 mg) in 1,2-Dichloro-ethane (5 mL) and cool in an ice bath. Add 1-chloroethyl chloroformate (1.2 equiv, 0.794 mmol; 0.086 mL). Stir the reaction 10 minutes in an ice bath then heat to reflux for 20 minutes and evaporate to dryness. Dissolve the residue in methanol (5 mL) and reflux for 45 minutes and evaporate to dryness to give 268 mg (0.779 mmol, 118%) 4-[4-(3-chloro-4-fluoro-phenyl)-1-ethyl-1H-imidazol-2-yl]-piperidine hydrochloride. cool in an ice bath the reaction 10 minutes in an ice bath then heat to reflux for 20 minutes evaporate to dryness Dissolve the residue in methanol (5 mL) reflux for 45 minutes evaporate to dryness

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

Procedure: A solution of the above aldehyde (1.17 g, 4 mmol), distilled 1,8-diamino naphthalene (0.63 g, 4 mmol), p-toluenesulfonic acid (10 mg), and tetrahydrofuran (6 mL) was stirred for 0.5 h at room temperature. The mixture was basified with 1 mL saturated sodium carbonate, diluted with THF-ether (1:1) and washed with water. The extract was concentrated and the residual solid was recrystallized from THF-ether (1:1, 30 mL) to give the 2,3-dihydroperimidine (1.50 g, 87%): mp 165-167° C.; 1H NMR (CDCl3) 7.59(s, 4H), 7.45 and 6.9(2d, 4H), 7.1(m, 4H), 6.4(d, 2H), 4.7(bs, 2H), 4.45(t, 1H), 4.0(t, 2H), 2.0-1.5(m, 8H); IR 3385, 3360, 2225, 1601 cm-1. washed with water The extract was concentrated the residual solid was recrystallized from THF-ether (1:1, 30 mL)

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

Procedure: A solution of the above aldehyde (1.17 g, 4 mmol), distilled 1,8-diamino naphthalene (0.63 g, 4 mmol), p-toluenesulfonic acid (10 mg), and tetrahydrofuran (6 mL) was stirred for 0.5 h at room temperature. The mixture was basified with 1 mL saturated sodium carbonate, diluted with THF-ether (1:1) and washed with water. The extract was concentrated and the residual solid was recrystallized from THF-ether (1:1, 30 mL) to give the 2,3-dihydroperimidine (1.50 g, 87%): mp 165-167° C.; 1H NMR (CDCl3) 7.59(s, 4H), 7.45 and 6.9(2d, 4H), 7.1(m, 4H), 6.4(d, 2H), 4.7(bs, 2H), 4.45(t, 1H), 4.0(t, 2H), 2.0-1.5(m, 8H); IR 3385, 3360, 2225, 1601 cm-1. washed with water The extract was concentrated the residual solid was recrystallized from THF-ether (1:1, 30 mL)

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 250 g of phenol are melted at about 60° C. 47.4 g of 1,8-diaminonaphthalene and 59.4 g of 1,8-naphthalic acid anhydride are introduced, while passing over nitrogen, and the mixture is heated to 150° C. in the course of 1 hour and kept at this temperature for 2 hours. The reaction mixture is cooled to 80° C., 120 ml of methanol are added at a temperature of 80° to 65° C. in the course of 30 minutes, and the mixture is cooled to room temperature and filtered with suction. After the residue has been washed with 240 ml of methanol and dried at 150° C., 88.8 g of the stated dyestuff are obtained in a very good quality. The reaction mixture is cooled to 80° C. the mixture is cooled to room temperature filtered with suction After the residue has been washed with 240 ml of methanol dried at 150° C. 88.8 g of the stated dyestuff are obtained in a very good quality

Conditions: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 250 g of phenol are melted at about 60° C. 47.4 g of 1,8-diaminonaphthalene and 59.4 g of 1,8-naphthalic acid anhydride are introduced, while passing over nitrogen, and the mixture is heated to 150° C. in the course of 1 hour and kept at this temperature for 2 hours. The reaction mixture is cooled to 80° C., 120 ml of methanol are added at a temperature of 80° to 65° C. in the course of 30 minutes, and the mixture is cooled to room temperature and filtered with suction. After the residue has been washed with 240 ml of methanol and dried at 150° C., 88.8 g of the stated dyestuff are obtained in a very good quality. The reaction mixture is cooled to 80° C. the mixture is cooled to room temperature filtered with suction After the residue has been washed with 240 ml of methanol dried at 150° C. 88.8 g of the stated dyestuff are obtained in a very good quality

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

Procedure: A mixture of 1.58 g of 1,8-diaminonaphthalene, 10.8 g of diethyl ketone, and 25 mg of p-toluenesulfonic acid monohydrate was heated and stirred for 5 hours in a steam bath and extracted with 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate water. The solvent was distilled off, yielding 20 g of 2,2-diethyl-2,3-dihydroperimidine. was heated extracted with 100 ml of ethyl acetate and 50 ml of saturated sodium bicarbonate water The solvent was distilled off

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

Procedure: A mixture of 79.1 g of 1,8-diaminonaphthalene, 57.4 g of 96% strength sulphuric acid and 700 ml of water is initially introduced into the reaction vessel at 50° C., and 57.8 g of hydroxy acetone are metered in over a period of 10 minutes. The mixture is then subsequently stirred at 50° C. for 2 hours and cooled to 0° C., and the product is isolated by filtration and dried at 70° C. in vacuo. is initially introduced into the reaction vessel at 50° C. are metered in over a period of 10 minutes cooled to 0° C. the product is isolated by filtration dried at 70° C. in vacuo

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

Procedure: A mixture of 79.1 g of 1,8-diaminonaphthalene, 57.4 g of 96% strength sulphuric acid and 700 ml of water is initially introduced into the reaction vessel at 50° C., and 57.8 g of hydroxy acetone are metered in over a period of 10 minutes. The mixture is then subsequently stirred at 50° C. for 2 hours and cooled to 0° C., and the product is isolated by filtration and dried at 70° C. in vacuo. is initially introduced into the reaction vessel at 50° C. are metered in over a period of 10 minutes cooled to 0° C. the product is isolated by filtration dried at 70° C. in vacuo

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

Procedure: 1,8-Diaminonaphthalene (1.04 grams; 0.00656 mole) and p-pentafluoroethoxybenzoyl chloride (1.8 grams; 0.00656 mole) were reacted in the procedures of Example 3, yielding 2.25 grams of product (82.7% yield), m.p., 240° C. (dec.), mass spectrum m/e 378.

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

Procedure: 1,8-Diaminonaphthalene (1.52 grams; 0.0096 mole) was dissolved in 25 ml. of toluene, then decanted. p-Trifluoromethoxybenzoyl fluoride (2.0 grams; 0.0096 mole) was dissolved in 25 ml. of toluene. Both solutions were added simultaneously to 25 ml. of toluene. After the reaction mixture had been stirred for approximately 4 hours, TLC indicated that the reaction was complete. of toluene, then decanted Both solutions were added simultaneously to 25 ml

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

Procedure: 1,8-Diaminonaphthalene (1.52 grams; 0.0096 mole) was dissolved in 25 ml. of toluene, then decanted. p-Trifluoromethoxybenzoyl fluoride (2.0 grams; 0.0096 mole) was dissolved in 25 ml. of toluene. Both solutions were added simultaneously to 25 ml. of toluene. After the reaction mixture had been stirred for approximately 4 hours, TLC indicated that the reaction was complete. of toluene, then decanted Both solutions were added simultaneously to 25 ml