Acetic Acid → 3-Cyano-2-pyridone

Sodium ethanolate (9.48 mL; 21 weight 0; 1.0 equiv.) was added to a solution of preceding methylene-dimethylamino (see 1.3.) (10 g; 1.0 equiv.) and cyanoacetamide (2.135 g; 1.0 equiv.) in ethanol (100 mL). The mixture was left under agitation 3 hours at ambient temperature. The medium was then neutralised with the dropwise addition of acetic acid and concentrated under reduced pressure. The reaction medium was diluted in ethyl acetate (200 mL) and the organic phase washed with a brine solution (150 mL). The organic phase was dried over magnesium sulfate, filtered and the solvents evaporated under reduced pressure. The residue was purified on silica gel (CH2Cl2/AcOEt 8:2) to give the pyridone with a global yield of 57%.

1. concentrationconcentrated under reduced pressure
2. additionThe reaction medium was diluted in ethyl acetate (200 mL)
3. washthe organic phase washed with a brine solution (150 mL)
4. dry with materialThe organic phase was dried over magnesium sulfate
5. filtrationfiltered
6. customthe solvents evaporated under reduced pressure
7. customThe residue was purified on silica gel (CH2Cl2/AcOEt 8:2)

ORD record

ord-f6ecba89f6884f5db1a4a859317d7a36

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09416143B2