2,6-Lutidine → HCID 54225306, compound

HRID 431031Notes

Reaction equation

HRID 431031 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][CH:12]=[C:11]([CH:15]=O)[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:11]2[CH:10]=[N:9][CH:14]=[CH:13][CH:12]=2)[N:3]=1

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 54225306HCID 54225306, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2,6-dimethyl pyridine (5.8 ml, 50 mMol), pyridine-3-carbaldehyde (4.9 ml, 52 mMol) in acetic anhydride (9.5 ml) is heated under reflux for 10 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 9:1 (7 L), then with toluene/acetone 4:1 (5 L) and finally with toluene/acetone 2:1 (5 L). The fractions containing the desired compound are combined, and evaporated in vacuo. The solid residue is recrystallized from methylene chloride/diisopropyl ether and 4.28 g of a colorless oil which solidify upon standing at 6-8° C.

Workup

  1. temperatureunder reflux for 10 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 9:1 (7 L)
  5. additionThe fractions containing the desired compound
  6. customevaporated in vacuo
  7. customThe solid residue is recrystallized from methylene chloride/diisopropyl ether and 4.28 g of a colorless oil which
  8. customupon standing at 6-8° C.

Sources & evidence

ORD record
ord-42451f967649462792b9612cf8686dbc
Source dataset
uspto-grants-2003_12
Patent number
US06656957B1

Reaction notes

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