Acetic Acid → HCID 59377437, compound

4-Fluorophenylmagnesium bromide (2M in THF; 130 ml) was added dropwise at 0° C. to a stirring solution of 6-chloronicotinic acid (12.92 g) in 150 mL of THF. After the addition was complete the reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was cooled to −60° C. and acetic acid (105 ml) was added dropwise, resulting in formation of a solid. After the addition was complete the reaction mixture was warmed to ambient temperature. The reaction mixture was then cooled to 0° C. and quenched by addition of saturated aqueous ammonium chloride solution. The mixture was partitioned between water and ethyl acetate, and the organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was dissolved in hot ethyl acetate. Upon standing a solid precipitate formed, which was collected and dried to give 10.04 g of 4-(4-fluoro-phenyl)-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid.

1. additionAfter the addition
2. temperatureThe reaction mixture was cooled to −60° C.
3. customresulting in formation of a solid
4. additionAfter the addition
5. temperaturewas warmed to ambient temperature
6. temperatureThe reaction mixture was then cooled to 0° C.
7. customquenched by addition of saturated aqueous ammonium chloride solution
8. customThe mixture was partitioned between water and ethyl acetate
9. customthe organic layer was separated
10. washwashed with water and brine
11. dry with materialdried over Na2SO4
12. filtrationfiltered
13. concentrationconcentrated under reduced pressure
14. dissolutionThe residue was dissolved in hot ethyl acetate
15. customformed
16. customwhich was collected
17. customdried

ORD record

ord-ae0ac4b6813649829b50165db73505ab

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08372865B2