N,N'-Dimethylethylenediamine → 1-(4-Nitrophenyl)-1H-pyridin-2-one

HRID 1665659Notes

Reaction equation

HRID 1665659 reaction equation
[NH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]1=[O:7].Br[C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.CNCCNC.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[Cu]I>[N+:15]([C:12]1[CH:13]=[CH:14][C:9]([N:1]2[CH:6]=[CH:5][CH:4]=[CH:3][C:2]2=[O:7])=[CH:10][CH:11]=1)([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 88712-PyridoneHCID 114661-Bromo-4-nitrobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 101982881-(4-Nitrophenyl)-1H-pyridin-2-oneYield 89%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 1H-pyridin-2-one (950 mg, 10 mmol), 1-bromo-4-nitro-benzene (2.4 g, 12 mmol) and CuI (400 mg, 2 mmol) in dioxane (15 mL) was stirred for 15 minutes. N,N′-dimethyl ethylenediamine (363 mg, 4 mmol) was then added, followed by the addition of K3PO4 (4.25 g, 20 mmol). The resulting mixture was heated to reflux at 110° C. for 2 hours under an atmosphere of nitrogen. The reaction mixture was then cooled to room temperature and poured onto ice. The resulting precipitate was filtered and purified by column chromatography using silica gel 60-120 mesh (50-100% ethyl acetate in hexane) to afford 1.86 g (89%) of 1-(4-nitro-phenyl)-1H-pyridin-2-one. 1H NMR: (DMSO-d6): δ 8.46 (d, 2H), 7.8 (m, 3H), 7.6 (t, 1H), 6.6 (d, 1H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. additionpoured onto ice
  4. filtrationThe resulting precipitate was filtered
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-5003a90e344f49dcb88dcfb97c6fb6e4
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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