Pyridine → HCID 136342782, compound

HRID 569574Notes

Reaction equation

HRID 569574 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].Cl.[CH3:19][O:20][NH2:21].N1C=CC=CC=1>CCO>[CH3:19][O:20][N:21]=[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

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 14152198HCID 14152198, compound

Product 1

HCID 136342782HCID 136342782, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-dihydro-6-methyl-2-oxo-5-(1-oxohexyl)-3-pyridinecarbonitrile (0.80 g, 0.0034 mol), methoxyamine hydrochloride (0.32 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-81667657a8e84f738eb96aaad805ec2f
Source dataset
uspto-grants-1988_03
Patent number
US04732982

Reaction notes

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