p-Toluenesulfonic acid → HCID 19753229, compound

HRID 483615Notes

Reaction equation

HRID 483615 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](C(OC)=O)[C:6]([C:9]([O:11][CH3:12])=[O:10])=[N:7][CH:8]=1)=[O:2].[C:17]1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:28]([OH:33])[CH2:29][CH2:30][CH2:31]O.[C:34](=[O:37])(O)[O-:35].[Na+]>C1(C)C=CC=CC=1>[O:33]1[CH2:28][CH2:29][CH2:30][CH2:31][O:2][CH:1]1[C:3]1[CH:4]=[CH:5][C:6]([C:9]([O:11][CH3:12])=[O:10])([C:34]([O:35][CH3:17])=[O:37])[NH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80641,4-ButanediolHCID 516892Sodium BicarbonateHCID 15672397HCID 15672397, compound

Product 1

HCID 19753229HCID 19753229, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 5-formyl-2,3-pyridinedicarboxylic acid, dimethyl ester, 5-dimethyl acetal (1.3 g, 0.0048 mol), a catalytic amount of p-toluenesulfonic acid, 1,4-butanediol and toluene is heated at reflux temperature for 2 hours and 30 minutes. The reaction mixture is cooled to room temperature, made basic with sodium bicarbonate and concentrated in vacuo to give a liquid. The liquid is partitioned between methylene chloride and 5% sodium bicarbonate solution. The layers are separated and the aqueous layer is extracted with methylene chloride, the combined methylene chloride extracts are dried over anhydrous magnesium sulfate and concentrated in vacuo to give an oil. The oil is chromatographed using silica gel and hexanes/ethyl acetate (2:1 to 1:1) as eluant to give the title compound as a clear oil (0.88 g, 62%), identified by IR and NMR spectral analyses.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. custom30 minutes
  3. concentrationconcentrated in vacuo
  4. customto give a liquid
  5. customThe liquid is partitioned between methylene chloride and 5% sodium bicarbonate solution
  6. customThe layers are separated
  7. extractionthe aqueous layer is extracted with methylene chloride
  8. dry with materialthe combined methylene chloride extracts are dried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. customto give an oil
  11. customThe oil is chromatographed

Sources & evidence

ORD record
ord-0401fdd216cc403ab43e0d852a1bf5df
Source dataset
uspto-grants-1993_07
Patent number
US05225564

Reaction notes

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