2,6-Lutidine → HCID 54066562, compound

HRID 431029Notes

Reaction equation

HRID 431029 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[C:9]([C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=O)#[N:10]>C(OC(=O)C)(=O)C>[CH3:8][C:4]1[N:3]=[C:2]([CH:1]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 79372,6-LutidineHCID 1012092-Cyanobenzaldehyde

Product 1

HCID 54066562HCID 54066562, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 2,6-dimethyl pyridine (5.8 ml, and 50 mMol), and 2-cyanobenzaldehyde (6.81 g, 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 400 g). The column is first eluted with toluene (400 ml) and then with toluene/ethyl acetate 95:5. The fractions containing the desired compound are combined, evaporated in vacuo. The solid residue is recrystallized from methylene chloride/diisopropyl ether and white crystals are isolated. (melting point: 113-114°).

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 400 g)
  4. washThe column is first eluted with toluene (400 ml)
  5. additionThe fractions containing the desired compound
  6. customevaporated in vacuo
  7. customThe solid residue is recrystallized from methylene chloride/diisopropyl ether and white crystals
  8. customare isolated

Sources & evidence

ORD record
ord-06543e42fede4dcba5e7dd6d5801316d
Source dataset
uspto-grants-2003_12
Patent number
US06656957B1

Reaction notes

Loading…