p-Fluoronitrobenzene → HCID 68539943, compound

HRID 1993530Notes

Reaction equation

HRID 1993530 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[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+]>CN1CCCC1.O.CCOC(C)=O>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2](=[O:1])[NH:3][CH:4]=2)=[CH:11][CH:12]=1)([O-:18])=[O:17]

Participants

7

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 178516290HCID 178516290, compound

Product 1

HCID 68539943HCID 68539943, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 84541-MethylpyrrolidineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2,5-dihydroxy-pyridine (4.65 g, 41.9 mmol), 4-fluoro-nitrobenzene (2.22 ml, 21 mmol) and Cs2CO3 (13.7 g, 41.9 mmol) in N-methyl-pyrrolidine (60 ml) is stirred for 18 h at 90° C. under N2-atmosphere. The reaction mixture is diluted with water and AcOEt, the aqueous layer separated off and extracted twice with AcOEt. The organic phases are washed with a NaHCO3 solution and brine, dried (Na2SO4) and partially concentrated. Thereby the title compound crystallizes and can be filtered off and washed with AcOEt: m.p.: 214-217° C.; 1H-NMR (DMSO-d6): 11.6 (s, HN), 8.22 (d, 2H), 7.57 (d, 1H), 7.43 (dd, 1H), 6.14 (d, 2H), 6.46 (d, 1H).

Workup

  1. customthe aqueous layer separated off
  2. extractionextracted twice with AcOEt
  3. washThe organic phases are washed with a NaHCO3 solution and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationpartially concentrated
  6. customThereby the title compound crystallizes
  7. filtrationcan be filtered off
  8. washwashed with AcOEt

Sources & evidence

ORD record
ord-a1a779bc0eee49f0a56f3e99064833dd
Source dataset
uspto-grants-2010_01
Patent number
US07652022B2

Reaction notes

Loading…