Sodium Iodide → Noradenalone hydrochloride

Temperature

40 °C

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.

1. temperatureThe mixture was refluxed for 24 hours
2. filtrationInsoluble substances in the reaction solution were filtered off
3. concentrationconcentrated under reduced pressure
4. additionEthyl acetate was added to the reaction solution
5. washwashed sequentially with water
6. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
7. distillationThe solvent was distilled off under reduced pressure
8. dissolutionThe oily residue was dissolved in 100 ml of methanol
9. addition13.6 ml of concentrated hydrochloric acid, and 1.5 g of a 10% palladium carbon catalyst was added
10. filtrationThe reaction solution was filtered
11. concentrationthe filtrate was concentrated under reduced pressure
12. additionTo the concentrated residue, acetone was added
13. filtrationthe precipitated crystals were collected by filtration

ORD record

ord-5fc28a9379414b758a2b0c538c963297

Source dataset

uspto-grants-1991_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05061794