Ammonium Acetate → 2,6-Bis(2-pyridyl)-4(1H)-pyridone

HRID 1373377

Reaction equation

HRID 1373377 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[CH2:8][C:9](=[O:19])[CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1)=O.C([O-])(=O)C.[NH4+:25]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:25][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][C:9](=[O:19])[CH:8]=1

Participants

4

Reactant 2

HCID 517165Ammonium AcetateHCID 113691811,5-Bis(2-pyridyl)-1,3,5-pentanetrione

Product 1

HCID 6193532,6-Bis(2-pyridyl)-4(1H)-pyridone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 10 g (37 mmol) of 1,5-di-pyridin-2-yl-pentane-1,3,5-trione and 20 g (260 mmol) of ammonium acetate is boiled under reflux in 250 ml of ethanol for 8 hours. The mixture so obtained is concentrated to about half its volume. After filtration, 1′H-[2,2′;6′,2″]terpyridine-4′-one is obtained in the form of a white solid. 1H-NMR (360 MHz, DMSO-d6): 7.40–7.50 (qm, 2H); 7.87 (s, 2H); 7.92–8.0 (tm, 2H); 8.57 (d, 2H, 7.7 Hz); 8.68 (d, 2H, J=4.5 Hz), 10.9 (s, 1H). MS (EI pos., 70 eV), m/z=249 (100, [M+]); 221 (40).

Workup

  1. customThe mixture so obtained
  2. concentrationis concentrated to about half its volume
  3. filtrationAfter filtration

Sources & evidence

ORD record
ord-4fba7bd191614fc09f9fdcd7b3658a5d
Source dataset
uspto-grants-2007_01
Patent number
US07161005B2

Linked notes

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