2-Chloronicotinic acid → HCID 22667896, compound

HRID 1355559Notes

Reaction equation

HRID 1355559 reaction equation
[Na].Cl[C:3]1[N:11]=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=[O:6]>C(O)CCC>[CH2:5]([O:6][C:3]1[C:4]([C:5]([OH:7])=[O:6])=[CH:8][CH:9]=[CH:10][N:11]=1)[CH2:4][CH2:8][CH3:9]

Participants

4

Reactant 2

HCID 762582-Chloronicotinic acidHCID 5360545Sodium

Product 1

HCID 22667896HCID 22667896, compoundYield 192.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Sodium (3.0 g, 130 mmol) was added to n-butanol (100 mL), and the mixture warmed to 80° C. until a solution was obtained, and then 2-chloro-nicotinic acid (10.0 g, 63.4 mmol) added, and the reaction heated under reflux for 4 hours. The cooled mixture (which solidified on cooling) was crushed and then partitioned between ethyl acetate and aqueous hydrochloric acid (sufficient to achieve pH 4), and the layers separated. The organic phase was washed with brine, and evaporated under reduced pressure. The residue was redissolved in ethyl acetate, dried (MgSO4) and re-evaporated to give the title compound as a solid (11.9 g, 96%).

Workup

  1. customwas obtained
  2. temperaturethe reaction heated
  3. temperatureunder reflux for 4 hours
  4. temperatureThe cooled mixture (which solidified on cooling)
  5. customwas crushed
  6. custompartitioned between ethyl acetate and aqueous hydrochloric acid (sufficient to achieve pH 4)
  7. customthe layers separated
  8. washThe organic phase was washed with brine
  9. customevaporated under reduced pressure
  10. dissolutionThe residue was redissolved in ethyl acetate
  11. dry with materialdried (MgSO4)
  12. customre-evaporated

Sources & evidence

ORD record
ord-e3a3afc8b13d4bf19f8daf85e521b8e6
Source dataset
uspto-grants-2003_07
Patent number
US06586439B2

Reaction notes

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