Nicotinic Acid → HCID 68983956, compound

HRID 1434896Notes

Reaction equation

HRID 1434896 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.O=S(Cl)[Cl:12].[CH2:14](O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C(Cl)(=O)C1C=CC=NC=1>C(Cl)(Cl)Cl>[ClH:12].[C:1]([O:9][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH3:14])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 24386Thionyl ChlorideHCID 684061-OctacosanolHCID 82604Nicotinoyl chloride

Product 1

HCID 68983956HCID 68983956, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Commercial SOCl2 (>99.5) and nicotinic acid (>99.5) were used without any further purification. To a three-necked flask was added nicotinic acid (16.9 g, 0.137 mol) under dry nitrogen atmosphere, and commercial SOCl2 (50 ml, 0.685 mol) was added dropwise. The mixture was heated to reflux for 3 hours and SOCl2 was evaporated under dry nitrogen atmosphere. After cooling to room temperature, 1-octacosanol (23.45 g, 0.057 mol) and CHCl3 (300 ml, dried anhydrous Na2SO4) were added to the nicotinic chloride and the mixture was heated to reflux for 4 hours. After cooling to room temperature overnight, the mixture was filtered under reduced pressure. The precipitate was dissolved in warm CHCl3 (800 ml) and then saturated NaHCO3 (100 ml) was added slowly. After stirring at room temperature for 1 hour, the organic layer was separated, washed with deionized water, brine and then dried over anhydrous Na2SO4. After the removal of the organic solvent, the residue was dissolved in warm CHCl3 (150 ml) and concentrated HCl (5 ml) was added with vigorous stirring for 30 minutes. The mixture was filtered under reduced pressure and the precipitate was washed with deoinized water, 95% EtOH, to obtain the product octacosanyl nicotinate hydrochloride (28.4 g, 90.3% yield, mp: 58-60° C.) as a pale yellow solid, and then re-crystallized with CHCl3 to give 24.3 g of octacosanyl nicotinate hydrochloride in yield 77.3%, mp: 74-75° C.

Workup

  1. customCommercial SOCl2 (>99.5) and nicotinic acid (>99.5) were used without any further purification
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 3 hours
  4. customSOCl2 was evaporated under dry nitrogen atmosphere
  5. temperaturethe mixture was heated
  6. temperatureto reflux for 4 hours
  7. temperatureAfter cooling to room temperature overnight
  8. filtrationthe mixture was filtered under reduced pressure
  9. dissolutionThe precipitate was dissolved in warm CHCl3 (800 ml)
  10. additionsaturated NaHCO3 (100 ml) was added slowly
  11. customthe organic layer was separated
  12. washwashed with deionized water, brine
  13. dry with materialdried over anhydrous Na2SO4
  14. customAfter the removal of the organic solvent
  15. dissolutionthe residue was dissolved in warm CHCl3 (150 ml)
  16. additionconcentrated HCl (5 ml) was added
  17. stirringwith vigorous stirring for 30 minutes
  18. filtrationThe mixture was filtered under reduced pressure
  19. washthe precipitate was washed with deoinized water, 95% EtOH

Sources & evidence

ORD record
ord-a30b3ee8dc4948af90e1abbede1ee14a
Source dataset
uspto-grants-2009_11
Patent number
US07615641B2

Reaction notes

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