Methyl iodide → HCID 57825894, compound

Methyl iodide (3 mL, 47.3 mmol) was added to a solution of 4-bromo-2-hydroxyacetophenone (9.25 g, 43 mmol) and potassium carbonate (6.54 g, 47.3 mmol) in acetone (20 mL) and the mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo to low volume and diluted with water. The aqueous mixture was extracted with dichloromethane (3×50 mL) and the combined organic solution was washed with water, dried over sodium sulfate and concentrated in vacuo. The residue was dissolved in 1,2-ethanediol (10 mL), hydrazine (19.47 mL, 400 mmol) and potassium hydroxide (7.86 g, 140 mmol) were added and the reaction mixture was heated at 150° C. for 60 hours. The reaction mixture was then quenched with 1M hydrochloric acid and extracted with ethyl acetate (3×20 mL). The combined organic solution was dried over sodium sulfate, concentrated in vacuo and the residue was purified by Kugel Rohr fractional distillation (150° C./0.05 mbar) to provide the title compound as a yellow oil (128 mg).

1. concentrationThe reaction mixture was concentrated in vacuo to low volume
2. additiondiluted with water
3. extractionThe aqueous mixture was extracted with dichloromethane (3×50 mL)
4. washthe combined organic solution was washed with water
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. dissolutionThe residue was dissolved in 1,2-ethanediol (10 mL)
8. temperaturethe reaction mixture was heated at 150° C. for 60 hours
9. customThe reaction mixture was then quenched with 1M hydrochloric acid
10. extractionextracted with ethyl acetate (3×20 mL)
11. dry with materialThe combined organic solution was dried over sodium sulfate
12. concentrationconcentrated in vacuo
13. distillationthe residue was purified by Kugel Rohr fractional distillation (150° C./0.05 mbar)

ORD record

ord-81b5c692c00547dc96619c7b7c4662a0

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08076356B2