Pyridine → HCID 136342783, compound

HRID 2073957Notes

Reaction equation

HRID 2073957 reaction equation
C([C:3]1([C:10](=O)[CH2:11][CH3:12])[CH2:8][NH:7][C:6](=[O:9])[CH:5]=[CH:4]1)C.Cl.[CH3:15][O:16][NH2:17].N1C=CC=[CH:20][CH:19]=1>CCO>[CH2:19]([C:8]1[NH:7][C:6](=[O:9])[CH:5]=[CH:4][C:3]=1[C:10](=[N:17][O:16][CH3:15])[CH2:11][CH3:12])[CH3:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 19762904HCID 19762904, compound

Product 1

HCID 136342783HCID 136342783, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-ethyl-5-(1-oxopropyl)-2(1H)-pyridinone (1.0 g, 0.0056 mol), methoxyamine hydrochloride (0.53 g, 0.0063 mol) and pyridine (3.0 ml) were heated and stirred at reflux for 48 hours in EtOH (30 ml). The reaction mixture was allowed to cool to room temperature and concentrated to a viscous liquid on the rotary evaporator at 60° C. The residue solidified on cooling. The solid was triturated with H2O (50 ml) and then collected by filtration to give 0.91 g, m.pt. 120°-125° C. One recrystallization (EtOH-H2O) gave 0.55 g (47%), m.pt. 129°-131° C.

Workup

  1. temperaturewere heated
  2. concentrationconcentrated to a viscous liquid on the rotary evaporator at 60° C
  3. temperatureon cooling
  4. customThe solid was triturated with H2O (50 ml)
  5. filtrationcollected by filtration
  6. customto give 0.91 g, m.pt. 120°-125° C
  7. customOne recrystallization (EtOH-H2O)
  8. customgave 0.55 g (47%), m.pt. 129°-131° C.

Sources & evidence

ORD record
ord-da887962c0c747aba27ce45bb9cc264f
Source dataset
uspto-grants-1990_04
Patent number
US04920229

Reaction notes

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