2-Chloronicotinic acid → HCID 22667896, compound

HRID 1633467Notes

Reaction equation

HRID 1633467 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 ethyl acetate and 2N hydrochloric acid (to give pH 3-4), and the layers separated. The organic phase was washed with brine, concentrated under reduced pressure, redissolved in ethyl acetate, dried (MgSO4) 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 ethyl acetate and 2N hydrochloric acid (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 ethyl acetate
  9. dry with materialdried (MgSO4)
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-58227a48a4f74f998db8e90b3bc2b4e3
Source dataset
uspto-grants-2003_01
Patent number
US06503908B1

Reaction notes

Loading…