| 92% |
With hydrazine hydrate; In ethylene glycol;Reflux; |
Step 2: Intermediate 2-1 (16.94 g, 60 mmol), ethylene glycol 150 mL, and 40 mL of 30% hydrazine hydrate were added to the reactor. After the reflux reaction was completed,The reaction solution was cooled, poured into water and filtered to afford Intermediate 2-2 (14.04 g, 92%). |
| 50% |
With hydrazine; In diethylene glycol; at 200℃; for 2h; |
Ten gram (0.035 mol) of Intermediate 2, 8.8 mL (0.175 mol) of hydrazine monohydrate, and 300 mL of diethylene glycol were added to a 1-L flask, and the whole was stirred under heat at 200C for 2 hours. After the completion of the reaction, water was added to the resultant, and the precipitate was separated by filtration. The coarse reaction product was reprecipitated with hexane and chloroform, whereby 4.5 g of Intermediate 3 (tan solid, 50% yield) as a target were obtained. |
| 50% |
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 200℃; for 2h; |
(1-3) Synthesis of Intermediate 3; Into a 1 liter flask, 10 g (0.035 moles) of Intermediate 2, 8.8 ml (0.175 moles) of hydrazine monohydrate, 12 g (0.18 moles) of potassium hydroxide and 300 ml of diethylene glycol were placed, and the obtained mixture was heated at 200 C. for 2 hours under stirring. After the reaction was completed, water was added, and the formed precipitates were separated by filtration. The crude reaction product was reprecipitated from hexane:chloroform, and 4.5 g of Intermediate 3 of the object compound was obtained (a light brown solid substance; the yield: 50%). |
| 50% |
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; |
In a 250 mL three-necked round bottom flask was added indenofluorenidione1.5 g (5.3 mmol),120 mLDiethylene glycol,Then add 7.5 g of KOH and 8 mL of 98% hydrazine monohydrateThe Then install a thermometer and a reflux condenser on a round bottom flask The temperature of the mixture is heated to 160 C, the temperature can not continue to rise, the heating reflux 24 h, the device is changed to a distillation device, the water generated in the reaction and the excess hydrazine hydrate are removed by distillation, and then the temperature is raised, The temperature was raised to 196 C and heated to reflux for 24 h. After the completion of the reaction, the hot reaction solution was poured into ice water mixed with dilute hydrochloric acid In the material, there are solid solids, standing for a while, the Buchner funnel filter the resulting gray solid, washed several times with water, and then the resulting solid Was added to glacial acetic acid to recrystallize, and finally a white solid indenofluorene 2a was obtained in 50% yield. |
| 50% |
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; |
In a 250 mL three-necked round bottom flask, 1.5 g (5.3 mmol) of indenovluidinedione and 120 mL of diethylene glycol were added followed by 7.5 g of KOH and 8 mL of 98% hydrazine monohydrate and a thermometer And the reflux condenser was heated slowly to the temperature of the mixture at 160 C. The temperature was unable to continue to rise. After heating for 24 hours, the apparatus was changed to a distillation apparatus, and the water generated in the reaction was distilled off. The amount of hydrazine hydrate, and then continue to heat up, the temperature rose to 196 C heating reflux reaction 24 h, after the end of the reaction of the hot reaction solution into dilute hydrochloric acid containing ice water mixture, solid production, standing for a while, The resulting solid was filtered through water and washed several times with water. The resulting solid was then recrystallized from glacial acetic acid and finally a white solid indenofluorene 2a was obtained in 50% yield. |
| 50% |
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 160 - 196℃; for 48h; |
The indenyl fluorenone was added to a 250 mL three-necked round bottom flask1.5 g (5.3 mmol),120 mL diethylene glycol,Then add 7.5 g of KOH and 8 mL of 98% hydrazine monohydrate.The thermometer and the reflux condenser were then placed on a round bottom flask,The temperature of the mixture is heated to 160 C and the temperature can not continue to rise,After heating for 24 h,The device is changed to a distillation unit,The water generated in the reaction and the excess hydrazine hydrate were distilled off,And then continue to heat up, the temperature rose to 196 C heating reflux reaction 24 h,After the completion of the reaction, the hot reaction solution was poured into ice water mixed with dilute hydrochloric acidIn the material, there are solid solids, standing for a while, the Buchner funnel filter the resulting gray solid, washed several times with water, and then the resulting solidWas added to glacial acetic acid to recrystallize, and finally a white solid indenofluorene 2a was obtained in 50% yield. |
|
With hydrazine hydrate; potassium hydroxide; In diethylene glycol; at 220℃; for 48h; |
Preparation of Compound (221); Compound (220) (12.0 g, 43.0 mmol) obtained as above was dissolved in diethylene glycol (140 mL), and potassium hydroxide (24.0 g, 425.0 mmol) and hydrazine hydrate (20.7 mL, 430 mmol) were added thereto. After stirring at 220 C. for 48 hours, the reaction mixture was cooled to 25 C., and 20% hydrochloric acid solution (400 mL) was added thereto. After stirring for 1 hour, the solid produced was filtered under reduced pressure. Acetone and tetrahydrofuran (200 mL each) were added to the solid, and the mixture was stirred for 20 hours, filtered under reduced pressure and dried under reduced pressure to obtain Compound (221) named as indenofluorene (8.5 g, 33.4 mmol). |
| 14.29 g |
With hydrazine hydrate; In ethylene glycol;Reflux; |
Add 1-1 (31.81 g, 100.00 mmol) to 50.0 mL of concentrated sulfuric acid,Stir at room temperature for 2 h,It was found that the color of the reaction solution turned yellow.Slowly add 300.0mL of water,Neutralize the reaction solution with sodium hydroxide to neutrality,There is solid precipitation,After cooling, suction filtration gave 1-2 (21.18 g, 75.56 mmol).Dissolve 1-2 in 150 ml of ethylene glycol,Add 40 ml of 30% hydrazine hydrate reflux reaction.The reaction solution is cooled and poured into water.The precipitate was filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).Dissolve 1-3 in 150 mL of toluene,Add 30g 1-4,1.5 g of tetrabutylammonium bromide,Reflux,Cooling filter column chromatography to obtain white powder(14.76 g, 47.55 mmol).Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform.Add 1.0g of anhydrous ferric chloride,20.0 mL of liquid bromine was added dropwise at zero, and the reaction was completed. The reaction solution was washed with a saturated solution of sodium sulfite and spun dry.A white solid intermediate A was obtained.Suggest an edit |
| 14.29 g |
With hydrazine hydrate; In ethylene glycol;Reflux; |
Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol).1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol).1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, it will be brominated,The white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After completion of the reaction, the reaction solution was washed with a saturated solution of sodium sulfite and dried to give a white solid (18.83). g, 40.22 mmol). |
| 14.29 g |
With hydrazine hydrate; In 1,2-dimethoxyethane;Reflux; |
The 2 - 1 (31.81 g, 100 . 00 mmol) adding 50.0 ml concentrated sulfuric acid, stirring at the room temperature 2 h, found that the color yellow reaction solution, slowly adding 300.0 ml water, sodium hydroxide and the reaction to reserve in neutral, solids are separated out, after cooling filtered to get solid 1 - 2 (21.18 g, 75 . 56 mmol). The 2 - 2 dissolved in 150 ml ethylene glycol, by adding 40 ml 30% hydrazine hydrate reflux reaction, but the reaction is poured into the water in the after cooling, filtration and precipitation to obtain white solid 2 - 3 (14.29 g, 56 . 12 mmol). The 1 - 3 is dissolved in 150 ml in toluene, adding 30 g 2 - 4, 1.5 g [...] bromination amine, reflux, cooling filtration column chromatography to obtain white powder (14.76 g, 47 . 55 mmol). Finally its bromo, the white powder dissolved in 100.0 ml in chloroform, adding 1.0 g anhydrous ferric chloride, zero dropwise 20.0 ml bromine, the reaction is completed, a sodium sulfite saturated solution many times reaction solution, turns on lathe does, to obtain white solid (18.83 g, 40 . 22 mmol). |
| 14.29 g |
With hydrazine hydrate; In diethylene glycol;Reflux; |
Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained |
| 14.29 g |
With hydrazine hydrate; In ethylene glycol;Reflux; |
Add 1-1 (31.81g, 100.00mmol) to 50.0mL concentrated sulfuric acid, stir at room temperature for 2h, and find that the color of the reaction solution turns yellow, slowly add 300.0mL water, then neutralize the reaction solution with sodium hydroxide to neutral, solid After precipitation, it was filtered with suction to give a solid 1-2 (21.18 g, 75.56 mmol). 1-2 was dissolved in 150 ml of ethylene glycol, and 40 ml of 30% hydrazine hydrate was added to reflux. The reaction mixture was cooled, poured into water, and filtered to give a white solid 1-3 (14.29 g, 56.12 mmol). 1-3 was dissolved in 150 mL of toluene, and 30 g of 1-4, 1.5 g of tetrabutylammonium bromide was added thereto, and the mixture was refluxed, and then filtered and purified to give white powder (14.76 g, 47.55 mmol). Finally, the bromination, the white powder was dissolved in 100.0 mL of chloroform, 1.0 g of anhydrous ferric chloride was added, and 20.0 mL of liquid bromine was added dropwise at zero degree. After the reaction was completed, the reaction solution was washed with a saturated solution of sodium sulfite, and dried. A white solid intermediate A (18.83 g, 40.22 mmol) was obtained. |
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