2-hydroxybenzohydrazide

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

Procedure: Following the general procedure of Example 1, condensation of 2-hydroxy-1-naphthaldehyde and salicylic hydrazide yielded a pale yellow solid (74%): mp 265° C.; 1H NMR d 12.32 (s, 1 H), 11.65 (br s, 1 H), 11.36 (br s, 1 H), 9.09 (s, 1 H), 7.84 (d, 1 H, J=7.5 Hz), 7.43 (m, 3 H), 7.13 (t, 1 H, J=6.0 Hz), 7.01 (t, 1 H, J=6.6 Hz), 6.83 (t, 1H, J=6.9 Hz), 6.77 (d, 1H, J=8.4 Hz), 6.57 (m, 2 H); 13C NMR d 163.72, 158.58, 157.88, 147.40, 133.75, 132.63, 131.42, 128.64, 128.49, 127.53, 127.44, 123.27, 120.65, 118.87, 118.61, 117.04, 115.35, 108.32; HRMS Calcd for C18H14N2O3 :306.1004, found 306.0985; Anal. (C18H14N2O3) C, H, N.

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 50 ml of N-dimethylacetamide were added 5.0 g of salicyloylhydrazine and 5.5 g of cinnamoyl chloride, and the mixture was stirred at 20° C for 9 hours. The reaction mixture was then poured into 2 liters of water, and the produced precipitate was collected by filtration and washed with water. The so obtained product was then recrystallized twice from acetic acid and dried under reduced pressure to yield 3 g of N-cinnamoyl-N'-salicyloylhydrazine as white crystals, m.p. 271° C. Analysis: Calculated for C16H14N2O3 ; C, 68.09%, H, 4.96%; N, 9.93%, Found: C, 68.08%; H, 4.81%; N, 9.08%. the produced precipitate was collected by filtration washed with water The so obtained product was then recrystallized twice from acetic acid dried under reduced pressure

Conditions: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 50 ml of N-dimethylacetamide were added 5.0 g of salicyloylhydrazine and 5.5 g of cinnamoyl chloride, and the mixture was stirred at 20° C for 9 hours. The reaction mixture was then poured into 2 liters of water, and the produced precipitate was collected by filtration and washed with water. The so obtained product was then recrystallized twice from acetic acid and dried under reduced pressure to yield 3 g of N-cinnamoyl-N'-salicyloylhydrazine as white crystals, m.p. 271° C. Analysis: Calculated for C16H14N2O3 ; C, 68.09%, H, 4.96%; N, 9.93%, Found: C, 68.08%; H, 4.81%; N, 9.08%. the produced precipitate was collected by filtration washed with water The so obtained product was then recrystallized twice from acetic acid dried under reduced pressure

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

Procedure: A mixture of 3.8 g (0.025 mole) salicoylhydrazine and 10 ml (14.3 g, 0.08 mole) methyl 2,2,2-trichloroacetimidate was stirred 16 hours at room temperature. The solid that formed was washed with petroleum ether and dried to give 7.5 g (100% Yield; mp 168°-169° C.). The structure was confirmed via infrared and elemental analysis. The solid that formed was washed with petroleum ether dried to give 7.5 g (100% Yield; mp 168°-169° C.)

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

Procedure: A four neck flask (1 liter) equipped with a thermometer and a stirrer was charged with 60.8 g (0.4 mol) of salicylohydrazide, 49.2 g (0.6 mol) of sodium acetate and 700 ml of acetic acid. Dropwise added thereto was 67.4 g (0.48 mol) of benzoyl chloride in one hour while stirring, and stirring was continued at room temperature (20° C.) for 3 hours. After finishing the reaction, 1.5 liter of deionized water was added and crystal was filtered off. After washing sufficiently the crystal with 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal. A four neck flask (1 liter) equipped with a thermometer and a stirrer Dropwise added in one hour stirring was continued at room temperature (20° C.) for 3 hours was added crystal was filtered off After washing sufficiently the crystal with 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal

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

Procedure: A four neck flask (1 liter) equipped with a thermometer and a stirrer was charged with 60.8 g (0.4 mol) of salicylohydrazide, 49.2 g (0.6 mol) of sodium acetate and 700 ml of acetic acid. Dropwise added thereto was 67.4 g (0.48 mol) of benzoyl chloride in one hour while stirring, and stirring was continued at room temperature (20° C.) for 3 hours. After finishing the reaction, 1.5 liter of deionized water was added and crystal was filtered off. After washing sufficiently the crystal with 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal. A four neck flask (1 liter) equipped with a thermometer and a stirrer Dropwise added in one hour stirring was continued at room temperature (20° C.) for 3 hours was added crystal was filtered off After washing sufficiently the crystal with 500 ml of methanol, it was dried under reduced pressure to obtain slightly brown crystal

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

Procedure: A four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer was charged with 76.1 g (0.5 mol) of salicylohydrazide and 1 liter of methanol, and 57.6 g (0.6 mol) of furfural was dropwise added thereto in 30 minutes while stirring at room temperature. After heating under reflux for 2 hours, the reaction liquid was cooled down to 20° C. or lower, and crystal was filtered off. The crystal was washed with a small amount of methanol and then dried under reduced pressure, whereby the intended compound (slightly yellow crystal) was obtained. The amount yielded in this reaction was 108.1 g (0.47 mol), and the yield was 93%. A four neck flask (2 liters) equipped with a thermometer, a reflux condenser and a stirrer was dropwise added After heating under reflux for 2 hours the reaction liquid was cooled down to 20° C. lower, and crystal was filtered off The crystal was washed with a small amount of methanol dried under reduced pressure, whereby the intended compound (slightly yellow crystal) was obtained The amount yielded in this reaction

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

Procedure: Following the general method as outlined in Example 1, into a suspension of 5-iodo-1H-indole-2,3-dione in acetic acid was added 2-hydroxybenzohydrazide. After stirring at 100° C., the reaction mixture was cooled to rt and a yellow solid precipitated out. Filtration on a fritté, washing with AcOH, water and drying under vacuo at 60° C. overnight gave 344 mg of the title compound (84%) as a yellow solid in 98.5% purity by HPLC (Rt: 4.61, gradient of 10 min, MaxPlot detection between 230 and 400 nm). the reaction mixture was cooled to rt a yellow solid precipitated out Filtration on a fritté washing with AcOH, water drying under vacuo at 60° C. overnight

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

Procedure: 152 parts by weight salicyclic acid hydrazide was heated with 152 parts by weight salicylic-acid methyl ester and 3 parts by weight boron trioxide in 230 parts by weight paraffin (viscosity at 60° C.: 100 m Pa s) to 140° to 150° C. while stirring vigorously. Methanol produced during the reaction was distilled off by a column. After about 3 hours, the reaction was completed. The now viscous reaction mixture was cooled down to 50° to 60° C., treated with alcohol (methanol or ethanol) and the mixture was stirred very vigorously at about 50° to 60° C. The yellow-colored alcohol phase was decanted from the viscous paste and the process was repeated until discoloration was complete. After separating the washing alcohol, drying in a vacuum at about 100° C. was performed. 460 parts by weight of a colorless viscous paste was obtained, consisting of 230 parts by weight N,N'-bis(salicyloyl)hydrazine (85% yield) and 230 parts by weight paraffin. By dissolving the paraffin with methylene chloride and boiling-out the solid matter with methanol, N,N'-bis(salicyloyl)hydrazine with a melting and decomposition range of 305° to 310° C. was obtained. was distilled off by a column The now viscous reaction mixture was cooled down to 50° to 60° C. treated with alcohol (methanol or ethanol) the mixture was stirred very vigorously at about 50° to 60° C The yellow-colored alcohol phase was decanted from the viscous paste After separating the washing alcohol drying in a vacuum at about 100° C. 460 parts by weight of a colorless viscous paste was obtained

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

Procedure: 90 g (0.6 mole) of salicylic acid hydrazide and 388.8 g (2.4 moles) of triethyl orthoacetate in 500 ml of n-propanol are refluxed for 84 hours. When the mixture has cooled, the precipitate is filtered off and recrystallized from a mixture of toluene and petroleum ether. 47 g of colorless crystals (26.7% of theory) are obtained; melting point 74°-76° C. When the mixture has cooled the precipitate is filtered off recrystallized from a mixture of toluene and petroleum ether

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

Procedure: 90 g (0.6 mole) of salicylic acid hydrazide and 355.2 g (2.4 moles) of orthoformic acid ethyl ester are refluxed for 22 hours. Excess of the ester is distilled off and the solid residue is recrystallized from ethanol. 62.9 g of colorless crystals (64.7% of theory) are obtained; melting point 112°-113° C. Excess of the ester is distilled off the solid residue is recrystallized from ethanol

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 g of salicylhydrazide in 100 ml of p-dioxane was added dropwise 13.1 g of trichloromethyl chloroformate while maintaining the temperature at 20°-30° C. with external cooling. After stirring at 25° C. for 0.5 hours, the suspension was refluxed for 4 hours then cooled to 25° C. and poured into excess ice-water. The mixture was filtered and the residue was recrystallized from acetonitrile to yield 9.0 g of the subject compound; m.p. 198°-200° C. while maintaining the temperature at 20°-30° C. with external cooling the suspension was refluxed for 4 hours then cooled to 25° C. The mixture was filtered the residue was recrystallized from acetonitrile