p-Fluoronitrobenzene → Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

HRID 13501

Reaction equation

HRID 13501 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([OH:11])[CH:10]=1)=[O:4].C[Si]([N-][Si](C)(C)C)(C)C.[K+].F[C:23]1[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][CH:8]=[C:9]([O:11][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)[CH:10]=1)=[O:4]

Participants

6

Reactant 4

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 354317Methyl 5-hydroxypyridine-3-carboxylateHCID 3251421Potassium bis(trimethylsilyl)amide

Product 1

HCID 22040734Methyl 5-(4-nitrophenoxy)pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

The mixture containing methyl-5-hydroxypyridine-3-carboxylate (1 eq), Potassium bis(trimethylsilyl)amide (1.2 eq) was stirred in N,N-dimethylformamide for 2 hours at room temperature. To this mixture was added 1-fluoro-4-nitrobenzene (1.1 eq) and Potassium carbonate (1.2 eq) and stirred at 80° C. for 16 h. The reaction mixture was then concentrated and partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried, filtered and concentrated in vacuum to give brown solid. Purification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate. MS: MH+=274.

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum
  8. customto give brown solid
  9. customPurification on silica gel methyl-5-(4-nitrophenoxy)pyridine-3-carboxylate

Sources & evidence

ORD record
ord-827bc1173d3441568cf390f6559fafd8
Source dataset
uspto-grants-2010_06
Patent number
US07728010B2

Linked notes

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