2-Chloronicotinic acid → HCID 22667896, compound

HRID 1007147Notes

Reaction equation

HRID 1007147 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Na]>C(O)CCC>[CH2:4]([O:5][C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5])[CH2:3][CH2:7][CH3:8]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 5360545Sodium

Product 1

HCID 22667896HCID 22667896, compoundYield 192%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

2-Chloronicotinic acid (10.0 g, 63.5 mmol) was added to a solution of sodium (3 g, 130 mmol) in butanol (100 ml) at 80° C., and the resulting mixture heated under reflux for 4 hours. The reaction was allowed to cool, and partitioned between EtOAc and 2M HCl (to give pH 3-4), and the layers separated. The organic phase was washed with brine, concentrated under reduced pressure, redissolved in EtOAc, dried (MgSO4), filtered and evaporated under reduced pressure, to give the desired product as a solid (11.9 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 4 hours
  3. temperatureto cool
  4. custompartitioned between EtOAc and 2M HCl (to give pH 3-4)
  5. customthe layers separated
  6. washThe organic phase was washed with brine
  7. concentrationconcentrated under reduced pressure
  8. dissolutionredissolved in EtOAc
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-eb26cbf3c9164fa69e28cbd7700c92f8
Source dataset
uspto-grants-2004_09
Patent number
US06794387B2

Reaction notes

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