3-bromobenzohydrazide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: In a pressure vessel was suspended 3-bromobenzohydrazide (1.8 g, 8.37 mmol) in 14 ml acetic acid. 1,1,1-Triethoxyethane (4.6 ml, 25 mmol) was added and the reaction was stirred at 150° C. for 3 h. The solvent was concentrated under reduced pressure and the crude was washed with sodium bicarbonate and brine. The organic layer was dried over sodium sulphate, filtered and evaporated under reduced pressure. The residue was re-dissolved in dichloromethane, concentrated under reduced pressure and a solid was precipitated. This solid was washed with diethylether, filtered and dried in the vacuum oven at 40° C. to obtain 670 mg (35% yield) of the title compound. Purity 100%. In a pressure vessel was suspended The solvent was concentrated under reduced pressure the crude was washed with sodium bicarbonate and brine The organic layer was dried over sodium sulphate filtered evaporated under reduced pressure The residue was re-dissolved in dichloromethane concentrated under reduced pressure a solid was precipitated This solid was washed with diethylether filtered dried in the vacuum oven at 40° C.

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 3-bromobenzoate (2 g, 9.3 mmol) was dissolved in 25 ml ethanol. Hydrazine hydrate (4.5 ml, 92.9 mmol) was added and the reaction was stirred at 80° C. overnight. The reaction mixture was evaporated under reduced pressure and a white solid was formed. This solid was washed with water and diethyl ether and dried in the vacuum oven to afford 1.8 g (90% yield) of the title compound. Purity 100%. The reaction mixture was evaporated under reduced pressure a white solid was formed This solid was washed with water and diethyl ether dried in the vacuum oven

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Methyl 3-bromobenzoate (2 g, 9.3 mmol) was dissolved in 25 ml ethanol. Hydrazine hydrate (4.5 ml, 92.9 mmol) was added and the reaction was stirred at 80° C. overnight. The reaction mixture was evaporated under reduced pressure and a white solid was formed. This solid was washed with water and diethyl ether and dried in the vacuum oven to afford 1.8 g (90% yield) of the title compound. Purity 100%. The reaction mixture was evaporated under reduced pressure a white solid was formed This solid was washed with water and diethyl ether dried in the vacuum oven

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.00 g (23.3 mmol) of 3-bromobenzoic acid hydrazide are placed in 50 ml tetrahydrofuran at room temperature. 2.70 g (27.2 mmol) of isobutyl isocyanate, dissolved in 10 ml tetrahydrofuran, are rapidly added dropwise with stirring to this suspension. The mixture is firstly further stirred at room temperature and then allowed to stand overnight. The precipitate formed after addition of 100 ml diethyl ether is filtered off and then washed with diethyl ether. An initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained. The mother liquor is concentrated, and the residue again slurried in diethyl ether and filtered. After washing with diethyl ether and drying in vacuo, a further 5.62 g (77% of theory) of the target compound remain. are rapidly added dropwise The mixture is firstly further stirred at room temperature The precipitate formed is filtered off washed with diethyl ether An initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained The mother liquor is concentrated filtered After washing with diethyl ether drying in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 5.00 g (23.3 mmol) of 3-bromobenzoic acid hydrazide are placed in 50 ml tetrahydrofuran at room temperature. 2.70 g (27.2 mmol) of isobutyl isocyanate, dissolved in 10 ml tetrahydrofuran, are rapidly added dropwise with stirring to this suspension. The mixture is firstly further stirred at room temperature and then allowed to stand overnight. The precipitate formed after addition of 100 ml diethyl ether is filtered off and then washed with diethyl ether. An initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained. The mother liquor is concentrated, and the residue again slurried in diethyl ether and filtered. After washing with diethyl ether and drying in vacuo, a further 5.62 g (77% of theory) of the target compound remain. are rapidly added dropwise The mixture is firstly further stirred at room temperature The precipitate formed is filtered off washed with diethyl ether An initial quantity of 1.42 g (19% of theory) of the target compound is thus obtained The mother liquor is concentrated filtered After washing with diethyl ether drying in vacuo

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 200-mL three-neck flask were added 3.3 g (20 mmol) of 1-chloroisoquinoline, 4.3 g (20 mmol) of 3-bromobenzoylhydrazine, and 80 mL of para-xylene. This mixture was refluxed at 150° C. for 14 hours under a nitrogen stream. After a predetermined time elapsed, this mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The obtained solid was washed with toluene, a saturated aqueous solution of sodium hydrogen carbonate, and water. This solid was dried, so that the substance which was the object of the synthesis was obtained as 6.2 g of a pale yellow powder in 90% yield. this mixture was cooled to room temperature the precipitated solid was collected by suction filtration The obtained solid was washed with toluene This solid was dried, so that the substance which

反応条件: temp:150.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a 200-mL three-neck flask were added 3.3 g (20 mmol) of 1-chloroisoquinoline, 4.3 g (20 mmol) of 3-bromobenzoylhydrazine, and 80 mL of para-xylene. This mixture was refluxed at 150° C. for 14 hours under a nitrogen stream. After a predetermined time elapsed, this mixture was cooled to room temperature, and the precipitated solid was collected by suction filtration. The obtained solid was washed with toluene, a saturated aqueous solution of sodium hydrogen carbonate, and water. This solid was dried, so that the substance which was the object of the synthesis was obtained as 6.2 g of a pale yellow powder in 90% yield. this mixture was cooled to room temperature the precipitated solid was collected by suction filtration The obtained solid was washed with toluene This solid was dried, so that the substance which

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Subsequently, 5.0 g (23 mmol) of 3-bromobenzohydrazine obtained in (i) above was put in a 300-mL three-neck flask, 10 mL of N-methyl-2-pyrrolidone was added therein, and the mixture was stirred. Thereafter, a mixed solution of 10 mL of N-methyl-2-pyrrolidone and 3.2 mL (28 mmol) of benzoyl chloride was dripped to the above mixture through a 50-mL dropping funnel. After the dripping, the mixture was heated and stirred at 80° C. for 3 hours so as to be reacted. After the reaction, water was added to the reaction solution, and a solid was precipitated. The precipitated solid was collected by suction filtration to obtain another solid. The obtained solid was washed with approximately 1 L of water and collected by suction filtration. The collected solid was washed with methanol and collected by suction filtration; thus, 7.1 g of a white solid that was an object was obtained (yield: 96%). above was put in a 300-mL three-neck flask After the dripping, the mixture was heated stirred at 80° C. for 3 hours so as to be reacted was added to the reaction solution a solid was precipitated The precipitated solid was collected by suction filtration to obtain another solid The obtained solid was washed with approximately 1 L of water collected by suction filtration The collected solid was washed with methanol collected by suction filtration was obtained (yield: 96%)