去甲肾上腺素EP杂质B HCl

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. Insoluble substances in the reaction solution were filtered off and concentrated under reduced pressure. Ethyl acetate was added to the reaction solution, and washed sequentially with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added thereto. The mixture was stirred at 40° C. for 5 hours under hydrogen gas atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours Insoluble substances in the reaction solution were filtered off concentrated under reduced pressure Ethyl acetate was added to the reaction solution washed sequentially with water a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure The oily residue was dissolved in 100 ml of methanol 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. The insolubles in the reaction solution were removed by filtration, and the filtrate was concentrated under reduced pressure. To the reaction solution, ethyl acetate was added, and the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid. 1.5 g of 10% palladium carbon catalyst was added to the solution, and the mixture was stirred under heating at 40° C. under a hydrogen gas stream for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. To the concentrated residue, actone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours The insolubles in the reaction solution were removed by filtration the filtrate was concentrated under reduced pressure To the reaction solution, ethyl acetate was added the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the oily residue was dissolved in 100 ml of methanol 1.5 g of 10% palladium carbon catalyst was added to the solution The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, actone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. The insolubles in the reaction solution were removed by filtration, and the filtrate was concentrated under reduced pressure. To the reaction solution, ethyl acetate was added, and the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid. 1.5 g of 10% palladium carbon catalyst was added to the solution, and the mixture was stirred under heating at 40° C. under a hydrogen gas stream for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours The insolubles in the reaction solution were removed by filtration the filtrate was concentrated under reduced pressure To the reaction solution, ethyl acetate was added the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the oily residue was dissolved in 100 ml of methanol 1.5 g of 10% palladium carbon catalyst was added to the solution The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. The insolubles in the reaction solution were removed by filtration, and the filtrate was concentrated under reduced pressure. To the reaction solution, ethyl acetate was added, and the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid. 1.5 g of 10% palladium carbon catalyst was added to the solution, and the mixture was stirred under heating at 40° C. under a hydrogen gas stream for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours The insolubles in the reaction solution were removed by filtration the filtrate was concentrated under reduced pressure To the reaction solution, ethyl acetate was added the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the oily residue was dissolved in 100 ml of methanol 1.5 g of 10% palladium carbon catalyst was added to the solution The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. Insoluble substances in the reaction solution were filtered off and concentrated under reduced pressure. Ethyl acetate was added to the reaction solution, and washed sequentially with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added thereto. The mixture was stirred at 40° C. for 5 hours under hydrogen gas atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours Insoluble substances in the reaction solution were filtered off concentrated under reduced pressure Ethyl acetate was added to the reaction solution washed sequentially with water a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure The oily residue was dissolved in 100 ml of methanol 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. The insolubles in the reaction solution were removed by filtration, and the filtrate was concentrated under reduced pressure. To the reaction solution, ethyl acetate was added, and the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid. 1.5 g of 10% palladium carbon catalyst was added to the solution, and the mixture was stirred under heating at 40° C. under a hydrogen gas stream for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. To the concentrated residue, actone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours The insolubles in the reaction solution were removed by filtration the filtrate was concentrated under reduced pressure To the reaction solution, ethyl acetate was added the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the oily residue was dissolved in 100 ml of methanol 1.5 g of 10% palladium carbon catalyst was added to the solution The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, actone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. The insolubles in the reaction solution were removed by filtration, and the filtrate was concentrated under reduced pressure. To the reaction solution, ethyl acetate was added, and the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid. 1.5 g of 10% palladium carbon catalyst was added to the solution, and the mixture was stirred under heating at 40° C. under a hydrogen gas stream for 5 hours. The reaction solution was filtered, and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours The insolubles in the reaction solution were removed by filtration the filtrate was concentrated under reduced pressure To the reaction solution, ethyl acetate was added the mixture was washed sequentially with water and with a saturated sodium chloride aqueous solution dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure the oily residue was dissolved in 100 ml of methanol 1.5 g of 10% palladium carbon catalyst was added to the solution The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration

反应条件: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10 g (53.6 mmol) of 2-chloro-3',4'-dihydroxyacetophenone was dissolved in 50 ml of acetone, and 600 mg (4.0 mmol) of sodium iodide and 5.23 g (80.5 mmol) of sodium azide were added thereto. The mixture was refluxed for 24 hours. Insoluble substances in the reaction solution were filtered off and concentrated under reduced pressure. Ethyl acetate was added to the reaction solution, and washed sequentially with water and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The oily residue was dissolved in 100 ml of methanol and 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added thereto. The mixture was stirred at 40° C. for 5 hours under hydrogen gas atmosphere. The reaction solution was filtered and the filtrate was concentrated under reduced pressure. To the concentrated residue, acetone was added, and the precipitated crystals were collected by filtration to obtain 5.5 g (yield: 50.4%) of 2-amino-3',4'-dihydroxyacetophenone hydrochloride. The mixture was refluxed for 24 hours Insoluble substances in the reaction solution were filtered off concentrated under reduced pressure Ethyl acetate was added to the reaction solution washed sequentially with water a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate The solvent was distilled off under reduced pressure The oily residue was dissolved in 100 ml of methanol 13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added The reaction solution was filtered the filtrate was concentrated under reduced pressure To the concentrated residue, acetone was added the precipitated crystals were collected by filtration