Ethanol → HCID 136342782, compound

HRID 249094Notes

Reaction equation

HRID 249094 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[CH:4][C:3]=1[C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[N:18]1C=CC=CC=1.C[CH2:25][OH:26]>>[CH3:25][O:26][N:18]=[C:11]([C:3]1[CH:4]=[C:5]([C:9]#[N:10])[C:6](=[O:8])[NH:7][C:2]=1[CH3:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 702EthanolHCID 1049PyridineHCID 14152198HCID 14152198, compound

Product 1

HCID 136342782HCID 136342782, compound

Procedure

A mixture of 1,2-dihydro-6-methyl-2-oxo-5-(1-oxohexyl)-3-pyridinecarbonitrile (0.80 g, 0.0038 mol) and pyridine (2.0 ml) were heated and stirred at reflux overnight in EtOH (30.0 ml). The solution was allowed to cool to room temperature and the solvent was removed on the rotary evaporator. The pasty residue was triturated with H2O, filtered and recrystallized (EtOH-H2O) giving 0.5 g (56%) m.pt. 159°-165° C. One more recrystallization gave the analytical sample m.pt. 170°-171° C.

Workup

  1. temperaturewere heated
  2. customthe solvent was removed on the rotary evaporator
  3. customThe pasty residue was triturated with H2O
  4. filtrationfiltered
  5. customrecrystallized (EtOH-H2O)
  6. customgiving 0.5 g (56%) m.pt. 159°-165° C
  7. customOne more recrystallization
  8. customgave the analytical sample m.pt. 170°-171° C.

Sources & evidence

ORD record
ord-7c80ae31b96f451bb6aba2cb38b01941
Source dataset
uspto-grants-1993_05
Patent number
US05212315

Reaction notes

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