2,6-Lutidine → HCID 54492086, compound

A solution of 24 ml (200 mMol) of 2,6-dimethyl pyridine and 25.6 ml (207 mMol) of 3-bromobenzaidehyde in 38 ml of acetic anhydride is heated under reflux for 7.5 hours. The acetic anhydride is then evaporated in vacuo, and the residue is dissolved in 500 ml of 4N hydrochloric acid and twice extracted with 200 ml each of hexane. The water phase is then extracted four times with 300 ml each of tert.-butyl methyl ether. The combined organic phases are washed twice with 300 ml each of a saturated solution of NaHCO3 in water, then once with 300 ml of brine (300 ml), dried over sodium sulfate, filtrated and evaporated in vacuo yielding 4.2 g of the title compound as colorless crystals of melting point 58-590.

1. temperatureunder reflux for 7.5 hours
2. customThe acetic anhydride is then evaporated in vacuo
3. dissolutionthe residue is dissolved in 500 ml of 4N hydrochloric acid
4. extractiontwice extracted with 200 ml each of hexane
5. extractionThe water phase is then extracted four times with 300 ml each of tert.-butyl methyl ether
6. washThe combined organic phases are washed twice with 300 ml each of a saturated solution of NaHCO3 in water
7. dry with materialonce with 300 ml of brine (300 ml), dried over sodium sulfate
8. filtrationfiltrated
9. customevaporated in vacuo

ORD record

ord-18d33813833147bab13f5e7b4e2d13dd

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06656957B1