Water → HCID 57815289, compound

Temperature

95 °C

To a solution of 0.11 kg of 5-hydroxy-2-(hydroxymethyl)-1,4-dihydropyridin-4-one disodium salt in 600 mL of dimethyl sulfoxide, 0.25 kg of potassium carbonate and 81 mL of 1-bromo-3-chloropropane were added, and the mixture was stirred at 80 to 90° C. for 3 hours 20 minutes, at 90 to 100° C. for 45 minutes, and further at 80 to 95° C. for 5 hours. The reaction mixture was cooled to room temperature, water and chloroform were then added thereto, and the insoluble substance was filtered off. The organic layer was separated and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography using an eluent of chloroform:methanol=10:1 to obtain 31 g of (3,4-dihydro-2H-(1,4)dioxepino(2,3-c)pyridin-8-yl)methanol as a brown oily substance.

1. waitfurther at 80 to 95° C. for 5 hours
2. temperatureThe reaction mixture was cooled to room temperature
3. filtrationthe insoluble substance was filtered off
4. customThe organic layer was separated
5. extractionthe aqueous layer was extracted with chloroform
6. dry with materialthe resultant solution was dried over anhydrous magnesium sulfate
7. distillationthe solvent was distilled off under reduced pressure
8. customThe resultant residue was purified by silica gel column chromatography

ORD record

ord-caf2bd0a6bcb49e0823f815148b6c460

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367831B2