Acetic Anhydride → HCID 86756152, compound

HRID 1276547Notes

Reaction equation

HRID 1276547 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1.[C:9]([O:12]C(=O)C)(=[O:11])[CH3:10]>S(=O)(=O)(O)O.C(Cl)(Cl)Cl>[C:9]([OH:12])(=[O:11])[CH3:10].[C:9]([OH:12])(=[O:11])[CH3:10].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=[O:8])[CH:2]=1

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 86756152HCID 86756152, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6212ChloroformSolvent

Procedure

Pyridine-3-carboxaldehyde (5.45 g, 0.051 mol) was dissolved in an excess of acetic acid anhydride (10 ml) and 4 drops conc. sulfuric acid added under stirring. The resulting red mixture was allowed to react at 70-75° C. for 7 days. The cooled, black coloured reaction mixture was diluted with CHCl3, washed twice with 10% aqueous NaHCO3 and then several times with brine. The organic phase was dried (MgSO4) and evaporated. The black crude product was dissolved in CHCl3, and impurities precipitated as pentane was added. Precipitates were removed. The solution was evaporated and the residual product distilled (Kugelrohr) under reduced pressure (140° C./0.2 mbar) to give a colourless oil. 1H- and 13C NMR (CDCL3), d (ppm) rel. to TMS: 8.80, 8.68, 7.83 and 7.37 (m, 4×1H, Ar-H), 7.73 (s, 1H, CH(OAc)2) and 2.14 (s, 6H, CH3); 168.443 (C=O), 150.778, 148.154, 134.303, 131.172 and 123.253 (Ar), 87.988 (CH(OAc)2) and 20.587 (CH3).

Workup

  1. additionadded
  2. customto react at 70-75° C. for 7 days
  3. washwashed twice with 10% aqueous NaHCO3
  4. dry with materialThe organic phase was dried (MgSO4)
  5. customevaporated
  6. dissolutionThe black crude product was dissolved in CHCl3
  7. customimpurities precipitated as pentane
  8. additionwas added
  9. customPrecipitates
  10. customwere removed
  11. customThe solution was evaporated
  12. distillationthe residual product distilled (Kugelrohr) under reduced pressure (140° C./0.2 mbar)
  13. customto give a colourless oil

Sources & evidence

ORD record
ord-78180ce6a805414ba017362fc394868b
Source dataset
uspto-grants-2000_12
Patent number
US06166074

Reaction notes

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