Sodium Carbonate → 2-Chloro-3-octyl-6-(4-octyloxyphenyl)pyridine

HRID 1780544Notes

Reaction equation

HRID 1780544 reaction equation
[CH2:1]([C:9]1[C:10](=O)[NH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:17][CH:16]=2)=[CH:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O=P(Cl)(Cl)[Cl:33].C(=O)([O-])[O-].[Na+].[Na+]>>[Cl:33][C:10]1[C:9]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:14][CH:13]=[C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])=[CH:17][CH:16]=2)[N:11]=1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 190469563-octyl-6-(4-octyloxyphenyl)-1H-2-pyridone

Product 1

HCID 190469532-Chloro-3-octyl-6-(4-octyloxyphenyl)pyridine

Procedure

0.32 g (0.8 mmol) of 3-octyl-6-(4-octyloxyphenyl)-1H-2-pyridone are heated together with 15 ml of phosphorus oxytrichloride in a sealed tube at 200° C. for 3 hours. The reaction mixture is poured onto ice water, and the resulting mixture is made basic with sodium carbonate. Extraction of the aqueous phase with methylene chloride, washing of the organic phase with sodium chloride solution, drying over sodium sulfate, filtration, removal of the solvent by distillation and chromatography (silica gel, 8:2 hexane/ethyl acetate) give 0.22 g of 2-chloro-3-octyl-6-(4-octyloxyphenyl)pyridine. ##STR15##

Workup

  1. additionThe reaction mixture is poured onto ice water
  2. extractionExtraction of the aqueous phase with methylene chloride
  3. washwashing of the organic phase with sodium chloride solution
  4. dry with materialdrying over sodium sulfate, filtration, removal of the solvent by distillation and chromatography (silica gel, 8:2 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-976049ba478e4e3795c005d854371c91
Source dataset
uspto-grants-1997_05
Patent number
US05630962

Reaction notes

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