Water → 4-(4-Nitrophenoxy)pyridin-2(1H)-one

HRID 1993528Notes

Reaction equation

HRID 1993528 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][N:3]=1.F[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1.C([O-])([O-])=O.[Cs+].[Cs+].O>CN1CCCC1>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][C:6]2[CH:5]=[CH:4][NH:3][C:2](=[O:1])[CH:7]=2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 178516518HCID 178516518, compound

Product 1

HCID 685390724-(4-Nitrophenoxy)pyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 84541-MethylpyrrolidineSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 2,4-dihydroxy-pyridine (2.33 g, 21 mmol), 4-fluoro-nitrobenzene (2.22 ml, 21 mmol) and Cs2CO3 (10.2 g, 31.3 mmol) in N-methyl-pyrrolidine (30 ml) is stirred for 3 h at 100° C. under N2-atmosphere. The reaction mixture is poured into water and the precipitate filtered off and washed with water. The solid is dissolved in CH2Cl2/MeOH. Then SiO2 (≈20 g) is added and the mixture Is concentrated in vacuo. The resulting powder is put on top of a SiO2-column and eluted with toluene/AcOEt 3:1→AcOEt→AcOEt/EtOH 9:1, yielding the title compound: m.p.: 227-228° C.; 1H-NMR (DMSO-d6): 11.60 (s, HN), 8.31 (d, 2H), 7.47 (d, 1H), 7.39 (d, 2H), 6.07 (dd, 1H), 5.67 (d, 1H).

Workup

  1. filtrationthe precipitate filtered off
  2. washwashed with water
  3. dissolutionThe solid is dissolved in CH2Cl2/MeOH
  4. additionThen SiO2 (≈20 g) is added
  5. concentrationthe mixture Is concentrated in vacuo
  6. washeluted with toluene/AcOEt 3:1→AcOEt→AcOEt/EtOH 9:1

Sources & evidence

ORD record
ord-0f78d76bb18040d48915c482d73f2405
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

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