Hydrochloric Acid → HCID 58504280, compound

HRID 2407735Notes

Reaction equation

HRID 2407735 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:12])[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH2:13]([O-:15])[CH3:14].[Na+].Cl.[CH2:18](O)C>>[Cl:12][C:10]1[CH:9]=[C:4]([CH:3]=[C:2]([O:15][CH2:13][CH3:14])[N:11]=1)[C:5]([O:7][CH2:8][CH3:18])=[O:6]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 93237Methyl 2,6-dichloroisonicotinateHCID 2723922Sodium ethoxide

Product 1

HCID 58504280HCID 58504280, compound

Conditions

Temperature
70 °C

Procedure

Methyl 2,6-dichloroisonicotinate (2.62 g) was partially dissolved in ethanol (50 mL) and a freshly prepared solution of 0.72 mol/L solution of sodium ethanolate (17.7 mL) was added at room temperature and then heated at 70° C. for 3 hours. The reaction was neutralized by the addition of 2N hydrochloric acid (6.5 mL) and then concentrated. The resulting solid was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude reaction was purified by column chromatography using an eluant of 2-4% ethyl acetate/hexane to provide the title compound (1.7 g) with the following physical data.

Workup

  1. concentrationconcentrated
  2. customThe resulting solid was partitioned between ethyl acetate and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cf15ce13ad2b4982bba88dff89243908
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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