Pyridine → Nicotinic Acid

HRID 876639Notes

Reaction equation

HRID 876639 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C([OH:29])CCCCCCC/C=C\CCCCCCCC.N1C=CC=CC=1>CCCCCC>[C:2]([OH:9])(=[O:29])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 5284499Oleyl Alcohol

Product 1

HCID 938Nicotinic Acid

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Nicotinoyl chloride hydrochloride (17.8 g, 0.1 mol) and oleyl alcohol (26.85 g, 0.1 mol) were added into hexane (250 ml). Pyridine (15.8 g, 0.2 mol) was added to the stirred mixture over a period of 10 min, and the reaction mixture was stirred at room temperature for 24 h. Pyridine hydrochloride was removed by filtration and washed with hexane. The combined filtrate was extracted with water, dried over MgSO4 and evaporated to dryness. The residue was digested twice with acetonitrile, and the sticky residue was dried to give a clear water-like liquid which turned soap-like upon cooling (21.1 g, 56.5 mmol, 56.5%).

Workup

  1. customPyridine hydrochloride was removed by filtration
  2. washwashed with hexane
  3. extractionThe combined filtrate was extracted with water
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customthe sticky residue was dried
  7. customto give a clear water-like liquid which
  8. temperatureupon cooling (21.1 g, 56.5 mmol, 56.5%)

Sources & evidence

ORD record
ord-24e6eacb8abc465f9e5def1140df56da
Source dataset
uspto-grants-2015_03
Patent number
US08987263B2

Reaction notes

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