Acetic Acid → 1-(Pyridin-4-yl)butane-1,3-dione

HRID 326970

Reaction equation

HRID 326970 reaction equation
[C:1]([O:9]C)(=O)[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.C[O-].[Na+].[CH3:14][C:15]([CH3:17])=[O:16].C(O)(=O)C>C(OCC)C>[O:9]=[C:1]([C:2]1[CH:3]=[CH:4][N:5]=[CH:6][CH:7]=1)[CH2:14][C:15](=[O:16])[CH3:17]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 227085Methyl isonicotinateHCID 10942334Sodium Methoxide

Product 1

HCID 124183301-(Pyridin-4-yl)butane-1,3-dione

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of methyl isonicotinate (96.0 g, 0.7 mol) and sodium methoxide (45.4 g, 0.84 mol) in ethyl ether (1 l), acetone (81.3 g, 1.4 mol) was added dropwise at 25°~30° C. and stirring was continued for 2 hrs. under reflux. After cooling, acetic acid (50.4 g, 0.84 mol) was added to the reaction mixture, the organic layer was separated, washed twice with H2O, dried over anhydrous MgSO4 and evaporated. The residue (87.5 g) was distilled under reduced pressure to give the title compound as a pale yellow oil which solidified in the refrigerator; yield: 40.2 g; bp 135°~138° C./10 mmHg; mp 62°~64.5° C. (Lit. bp 118°~120° C.; mp 66.5°~67° C.; R. Levine, J. K. Sneed, J. Am. Chem. Soc., 73, 5614 (1951).). ##STR30##

Workup

  1. additionwas added dropwise at 25°~30° C.
  2. temperatureunder reflux
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed twice with H2O
  6. dry with materialdried over anhydrous MgSO4
  7. customevaporated
  8. distillationThe residue (87.5 g) was distilled under reduced pressure

Sources & evidence

ORD record
ord-bffd8543561940169d39de551465e1f7
Source dataset
uspto-grants-1993_12
Patent number
US05272036

Linked notes

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