2,6-Lutidine → HCID 53638878, compound

HRID 431030Notes

Reaction equation

HRID 431030 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[N:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1>C(OC(=O)C)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]=[CH:15][C:12]2[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=2)[N:3]=1

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 53638878HCID 53638878, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2,6-dimethyl pyridine (5.8 ml, and 50 mMol), and pyridine-4-carbaldehyde (4.9 ml, and 52 mMol) in acetic anhydride (9.5 ml) is heated under reflux for 16 hours. The acetic anhydride is then evaporated in vacuo and the residue purified on column chromatography (silica gel 900 g). The column is first eluted with toluene/acetone 4:1 (5 L), then with toluene/acetone 3:1 (5 L) and finally with toluene/acetone 2:1 (15 L). The fractions containing the desired compound are combined, evaporated in vacuo. The solid residue is recrystallized from methylene chloride/diisopropyl ether and 0.956 g of white crystals are isolated. (melting point: 72-73° C.).

Workup

  1. temperatureunder reflux for 16 hours
  2. customThe acetic anhydride is then evaporated in vacuo
  3. customthe residue purified on column chromatography (silica gel 900 g)
  4. washThe column is first eluted with toluene/acetone 4:1 (5 L)
  5. additionThe fractions containing the desired compound
  6. customevaporated in vacuo
  7. customThe solid residue is recrystallized from methylene chloride/diisopropyl ether and 0.956 g of white crystals
  8. customare isolated

Sources & evidence

ORD record
ord-75209e5806e54e63a35d3a1abfcc8a51
Source dataset
uspto-grants-2003_12
Patent number
US06656957B1

Reaction notes

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