Acetic Anhydride → HCID 54066562, compound

HRID 431028Notes

Reaction equation

HRID 431028 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:12]=[C:13]([CH:16]=[CH:17][CH:18]=1)C=O)#[N:10].[C:19](OC(=O)C)(=O)C>>[CH3:8][C:4]1[N:3]=[C:2]([CH:1]=[CH:19][C:12]2[CH:13]=[CH:16][CH:17]=[CH:18][C:11]=2[C:9]#[N:10])[CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 79372,6-LutidineHCID 90670m-Formylbenzonitrile

Product 1

HCID 54066562HCID 54066562, compound

Procedure

A solution of 2,6-dimethyl pyridine (4.2 ml, 36.28 mMol), 3-cyanobenzaldehyde (4.95 g, 37.74 mMol) in acetic anhydride (6.85 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, and evaporated in vacuo. The solid residue is recrystallized from methylene chloride/hexane and 3.18 g of white crystals are isolated. (melting point: 91-92°).

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/hexane and 3.18 g of white crystals
  8. customare isolated

Sources & evidence

ORD record
ord-81a283332dfc44ba80293d80b0e8dc05
Source dataset
uspto-grants-2003_12
Patent number
US06656957B1

Reaction notes

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