Formic Acid → 2-[1-(2,6-Diethylphenylimino)ethyl]-6-acetylpyridine

HRID 889549Notes

Reaction equation

HRID 889549 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10](=O)[CH3:11])[N:5]=1)(=[O:3])[CH3:2].[CH2:13]([C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:16]=1[NH2:17])[CH3:14].C(O)=O>CCCCCCC>[CH2:13]([C:15]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH3:23])[C:16]=1[N:17]=[C:10]([C:6]1[N:5]=[C:4]([C:1](=[O:3])[CH3:2])[CH:9]=[CH:8][CH:7]=1)[CH3:11])[CH3:14]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 113692,6-DiethylanilineHCID 707902,6-Diacetylpyridine

Product 1

HCID 221408662-[1-(2,6-Diethylphenylimino)ethyl]-6-acetylpyridineYield 41.6%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Procedure

10.35 g of 2,6-diacetylpyridine (0.0634 mol), 7.10 g of 2,6-diethylaniline (0.0476 mol) and 2 ml of formic acid were stirred in 300 ml of heptane at room temperature for 71 h. The insoluble solid was filtered off (11.10 g) and dissolved in 150 ml of toluene and the solution was extracted with 10 ml of a saturated Na2CO3 solution. The toluene phase was dried over Na2SO4 and filtered and the solvent was distilled off in vacuo. 5.58 g (0.0198 mol) of the product were obtained in a purity of 99% (GC/MS) in a yield of 40%. The mother liquor of the reaction solution was freed completely from the solvent and the residue was recrystallized from hot heptane. 2.00 g (0.0068 mol) of the product were additionally obtained in a purity of 100% (GC/MS). The total yield was 54%.

Workup

  1. filtrationThe insoluble solid was filtered off (11.10 g)
  2. dissolutiondissolved in 150 ml of toluene
  3. extractionthe solution was extracted with 10 ml of a saturated Na2CO3 solution
  4. dry with materialThe toluene phase was dried over Na2SO4
  5. filtrationfiltered
  6. distillationthe solvent was distilled off in vacuo

Sources & evidence

ORD record
ord-03576cda50b14d59a693a627eecb3764
Source dataset
uspto-grants-2012_08
Patent number
US08252875B2

Reaction notes

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