1-hydrazinylbutan-2-ol

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

Procedure: Into a flask equipped with a stirrer, heating mantle and Dean - Stark water separator is charged 7.2 g (0.30 mole) of a mixture of cis-and trans-2-p-chlorobenzoylcyclobutane carboxylic acid, 3.5 g (0.033 mole) of 1-hydrazino-2-butanol and 100 ml. of toluene. The mixture is stirred and refluxed until the water layer in the Dean-Stark tube remains constant (ca. 5hr). The solvent is removed in vacuo on a rotary evaporator, and the residue is dissolved in hot diethyl ether and allowed to cool to room temperature. The resultant solid is filtered off and yields 2-(p-chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one(isomer B;m.p. 133°-135°). The filtrate is further concentrated to give Isomer A (m.p. 115.5°-119° C). Into a flask equipped with a stirrer (ca. 5hr) The solvent is removed in vacuo on a rotary evaporator the residue is dissolved in hot diethyl ether The resultant solid is filtered off

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 75°-77° C) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin(2H)-3-one, (m.p. 108.5°-100° C) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 80°-81° C) respectively.

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 75°-77° C) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin(2H)-3-one, (m.p. 108.5°-100° C) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 80°-81° C) respectively.

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

Procedure: Into a flask equipped with a stirrer, heating mantle and Dean - Stark water separator is charged 7.2 g (0.30mole) of a mixture of cis-and trans-2-p-chlorobenzoylcyclobutane carboxylic acid, 3.5g(0.033 mole) of 1-hydrazino-2-butanol and 100 ml. of toluene. The mixture is stirred and refluxed until the water layer in the Dean-Stark tube remains constant (ca. 5 hr). The solvent is removed in vacuo on a rotary evaporator, and the residue is dissolved in hot diethyl ether and allowed to cool to room temperature. The resultant solid is filtered off and yields 2-(p-chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one(Isomer B;m.p. 133°-135°). The filtrate is further concentrated to give Isomer A (m.p. 115.5°-119° C.). Into a flask equipped with a stirrer (ca. 5 hr) The solvent is removed in vacuo on a rotary evaporator the residue is dissolved in hot diethyl ether The resultant solid is filtered off

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4 dichlorobenzoyl)-propionic acid and 1-hydrazino-2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one(m.p. 75°-77° C.) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin(2H)-3-one (m.p. 108.5°-100° C.) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one(m.p. 80°-81° C.) respectively.

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

Procedure: A mixture of 10 g. of 2-(m-trifluoromethylphenyl)-3-dimethylaminoacrolein, 5 g. of 2-hydroxybutylhydrazine and 100 ml. of benzene is refluxed for 2.5 hours. The benzene is evaporated off, ether added, and the reaction mixture cooled to obtain a precipitate which is recovered by filtering, washed with pentane, dissolved in methylene chloride, dried, treated with charcoal and filtered. The resulting solution is treated by addition of pentane and the resulting precipitate recovered by filtering, washed with pentane and dried under reduced pressure to obtain 1-(2-hydroxybutyl)-4-(m-trifluoromethylphenyl)-pyrazole, m.p. 77°-79°C. A mixture of 10 g The benzene is evaporated off ether added the reaction mixture cooled to obtain a precipitate which is recovered by filtering washed with pentane dissolved in methylene chloride dried treated with charcoal filtered The resulting solution is treated by addition of pentane the resulting precipitate recovered by filtering washed with pentane dried under reduced pressure

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

Procedure: Into a flask equipped with a stirrer, heating mantle and Dean-Stark water separator is charged 7.2 g (0.30 mole) of a mixture of cis-and trans-2-p-chlorobenzoylcyclobutane carboxylic acid, 3.5g(0.033 mole) of 1-hydrazino-2-butanol and 100 ml. of toluene. The mixture is stirred and refluxed until the water layer in the Dean-Stark tube remains constant (ca. 5 hr). The solvent is removed in vacuo on a rotary evaporator, and the residue is dissolved in hot diethyl ether and allowed to cool to room temperature. The resultant solid is filtered off and yields 2-(p-chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one (Isomer B;m.p. 133°-135°). The filtrate is further concentrated to give Isomer A (m.p. 115.5° - 119°C). Into a flask equipped with a stirrer (ca. 5 hr) The solvent is removed in vacuo on a rotary evaporator the residue is dissolved in hot diethyl ether The resultant solid is filtered off

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4 dichlorobenzoyl)-propionic acid and 1-hydrazino -2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl-4,5-dihydropyridazin (2H)-3-one(m.p. 75°-77°C) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 108.5° - 100°C) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one(m.p. 80°-81°C) respectively.

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-benzoyl-2-hydroxy-propionic acid and 1-hydrazino-2-hexanol or 3-benzoyl-2-hydroxy-propionic acid and 1-hydrazino-2-propanol or 3-benzoyl-2-hydroxy-3-methyl-propionic acid and butyl hydrazine in place of the 3-benzoyl-2-hydroxy-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 6-phenyl-2-(2-hydroxyhexyl)-4-hydroxy-4,5-dihydropyridazine-3(2H)-one; 6-phenyl-2-(2-hydroxypropyl)-4-hydroxy-4,5-dihydropyridazin-3(2H)-one; or 2-butyl-4,5-dihydro-4-hydroxy-5-methyl-6-phenylpyridazin-3(2H)-one (m.p. 129°-155° C.), respectively.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 3.5 grams (18 mmol) of 3-benzoyl-2-hydroxy-propionic acid and 1.9 grams (18 mmol) of 1-hydrazino-2-butanol in 40 ml of n-butanol is refluxed under nitrogen at 120° C. for 18 hours. After evaporation of the solvent, the product is partitioned between ether and water. The ether layer is washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and evaporated. The resulting residue is dissolved in 2% ethanol-chloroform and filtered through 200 grams of silica gel yielding after evaporation 4,5-dihydro-4-hydroxy-2-(2-hydroxybutyl)-6-phenylpyridazin-3(2H)-one, m.p. 92°-94° C. After evaporation of the solvent the product is partitioned between ether and water The ether layer is washed with aqueous sodium bicarbonate and brine dried over magnesium sulfate evaporated The resulting residue is dissolved in 2% ethanol-chloroform filtered through 200 grams of silica gel yielding after evaporation 4,5-dihydro-4-hydroxy-2-(2-hydroxybutyl)-6-phenylpyridazin-3(2H)-one, m.p. 92°-94° C.

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

Procedure: Into a flask equipped with a stirrer, heating mantle and Dean - Stark water separator is charged 7.2 g (0.30 mole) of a mixture of cis-and trans-2-p-chlorobenzoylcyclobutane carboxylic acid, 3.5 g (0.033 mole) of 1-hydrazino-2-butanol and 100 ml. of toluene. The mixture is stirred and refluxed until the water layer in the Dean-Stark tube remains constant (ca. 5hr). The solvent is removed in vacuo on a rotary evaporator, and the residue is dissolved in hot diethyl ether and allowed to cool to room temperature. The resultant solid is filtered off and yields 2-(p-chlorophenyl)-4-(2-hydroxybutyl) 3,4-diazabicyclo [4.2.0]-oct-2-ene-5-one(isomer B;m.p. 133°-135°). The filtrate is further concentrated to give Isomer A (m.p. 115.5°-119° C). Into a flask equipped with a stirrer (ca. 5hr) The solvent is removed in vacuo on a rotary evaporator the residue is dissolved in hot diethyl ether The resultant solid is filtered off

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

Procedure: When the above procedure is carried out using equivalent amounts of 3-(p-fluorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol,3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-propanol or 3-(3,4-dichlorobenzoyl)-propionic acid and 1-hydrazino-2-hexanol in place of the 3-(p-chlorobenzoyl)-propionic acid and 1-hydrazino-2-butanol used therein, there is obtained 3-(p-fluorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 75°-77° C) 3-(3,4-dichlorophenyl)-2-(2-hydroxypropyl)-4,5-dihydropyridazin(2H)-3-one, (m.p. 108.5°-100° C) or 3-(3,4-dichlorophenyl)-2-(2-hydroxyhexyl)-4,5-dihydropyridazin (2H)-3-one (m.p. 80°-81° C) respectively.