Hydrochloric Acid → HCID 11790587, compound

HRID 902010Notes

Reaction equation

HRID 902010 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]C#N)=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:17]([O:19]CC)=O.[O-]CC.[Na+].Cl>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 17307Ethyl 2-pyridinecarboxylateHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 2723922Sodium ethoxide

Product 1

HCID 11790587HCID 11790587, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

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

Workup

  1. temperatureto reflux for 2 hours
  2. additionpour onto ice
  3. customcollect the precipitate
  4. filtrationby vacuum filtration
  5. dissolutionDissolve the residue in 48% aqueous hydrobromic acid (25 mL)
  6. temperatureheat
  7. temperatureto reflux for 2 hours
  8. additionPour the solution onto ice
  9. extractionExtract the aqueous solution three times with CH2Cl2
  10. dry with materialdry (Na2SO4)
  11. filtrationfilter
  12. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-16b0b1d6da2e4356a4f109ee0a0edbe7
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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