Hydrogen Bromide → HCID 23700988, compound

A solution of sodium 3,4-methylenedioxy-phenoxide was prepared by adding slowly with stirring and under nitrogen a solution of 3,4-methylenedioxy phenol (59.66 g, 0.432 mole) in 250 ml of tetrahydrofuran (THF) (distilled from lithium aluminum hydride) to a mixture of sodium hydride (50%) (20.74 g, 0.432 mole), (previously washed with hexane and dried) in 250 ml of THF. After stirring for 30 min at room temperature, all evolution of hydrogen ceased and 1-(2'-pyridyl)-2-bromoethanol* hydrobromide (30.56 g, 0.108 mole) was added as a solid over a 5 min period. The reaction was heated at reflux overnight under nitrogen. The THF was removed in vacuo, and the resulting dark brown oil was partitioned between water and methylene chloride. The methylene chloride layer was extracted with 10% sodium hydroxide and was dried over sodium sulfate. The solvent was removed in vacuo to give a brown solid (21.95 g). This material was dissolved in methanol and converted to the hydrochloride salt with ethereal hydrogen chloride. This salt was recrystallized from methanol-diethyl ether to give 18.29 g (57.3%) of a brown solid, m.p. 165.6°-167.0° C. with decomposition.

1. additionby adding slowly
2. wash(previously washed with hexane
3. dry with materialdried) in 250 ml of THF
4. temperatureThe reaction was heated
5. temperatureat reflux overnight under nitrogen
6. customThe THF was removed in vacuo
7. customthe resulting dark brown oil was partitioned between water and methylene chloride
8. extractionThe methylene chloride layer was extracted with 10% sodium hydroxide
9. dry with materialwas dried over sodium sulfate
10. customThe solvent was removed in vacuo

ORD record

ord-6da7eb6b86e04b1f9dcc2727bc354a6d

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04835164