2,6-Diacetylpyridine → 2,6-Bis[1-(2-chloro-4,6-dimethylphenylimino)ethyl]pyridine

HRID 535250

Reaction equation

HRID 535250 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=O)[CH3:2].[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[NH2:16]>C(O)=O.CO>[Cl:13][C:14]1[CH:20]=[C:19]([CH3:21])[CH:18]=[C:17]([CH3:22])[C:15]=1[N:16]=[C:1]([C:4]1[N:5]=[C:6]([C:10](=[N:16][C:15]2[C:17]([CH3:22])=[CH:18][C:19]([CH3:21])=[CH:20][C:14]=2[Cl:13])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:2]

Participants

5

Reactant 2

HCID 707902,6-DiacetylpyridineHCID 1130332-Chloro-4,6-dimethylaniline

Product 1

HCID 580977402,6-Bis[1-(2-chloro-4,6-dimethylphenylimino)ethyl]pyridine

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent

Procedure

In a 200 ml round bottom flask, 2.0 g of 2,6-diacetylpyridine (M=163.176 g/mol, 0.0123 mol) and 75 ml of methanol were placed. Next 3.81 g of 2-chloro-4,6-dimethylaniline (M=155.627 g/mol, 0.0245 mole) and three drops of formic acid were added and the solution stirred at room temperature under nitrogen for four days, at which time no precipitate had formed. The reaction then was refluxed for 24 h. GC analysis indicated that the reaction was incomplete. Refluxing was continued for a total of 1 week. Solvent was stripped from the reaction mixture via rotary evaporator. Flash chromatography through a basic alumina column (eluted with hexane/ethyl acetate 20:1) lead to isolation of an oil. The oil was then crystallized from methanol/methylene chloride to receive pale yellow crystals.

Workup

  1. customhad formed
  2. customThe reaction
  3. temperaturethen was refluxed for 24 h
  4. temperatureRefluxing
  5. customwas continued for a total of 1 week
  6. customSolvent was stripped from the reaction mixture via rotary evaporator
  7. washFlash chromatography through a basic alumina column (eluted with hexane/ethyl acetate 20:1) lead to isolation of an oil
  8. customThe oil was then crystallized from methanol/methylene chloride

Sources & evidence

ORD record
ord-8404ac0767394c00841abdf971a0521d
Source dataset
uspto-grants-2014_10
Patent number
US08859451B2

Linked notes

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