Hydrochloric Acid → HCID 11790587, compound

Participants

Reaction Steps

Combine a solution of 4-fluorophenylacetonitrile (1.00 g, 7.4 mmol) and ethyl picolinate (1.12 g, 7.4 mmol) in absolute ethyl alcohol (15 mL) under N2 with 21 wt % sodium ethoxide solution in denatured ethyl alcohol (4.2 mL, 11.1 mmol) and heat to reflux for 2 hours, then pour onto ice. Adjust the pH to 4 with concentrated hydrochloric acid and collect the precipitate by vacuum filtration. Dissolve the residue in 48% aqueous hydrobromic acid (25 mL) and heat to reflux for 2 hours. Pour the solution onto ice and adjust the pH to 7 with 5N aqueous sodium hydroxide solution. Extract the aqueous solution three times with CH2Cl2. Combine the organic extracts, dry (Na2SO4), filter, and concentrate in vacuo to afford the title compound 668 mg (42%) as a brown amorphous solid. MS FAB+ m/z=216.1

Provenance & Evidence