Chlorobenzene → HCID 23153479, compound

HRID 492737Notes

Reaction equation

HRID 492737 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([OH:22])[CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20].ClC1C=CC=CC=1.CCCCCC>CN(C)C=O.CO.C(OCC)(=O)C>[F:12][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:18]=1[N+:19]([O-:21])=[O:20])[O:22][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([O:10][CH3:11])=[O:9])[CH:3]=1

Participants

8

Reactant 4

HCID 7964ChlorobenzeneHCID 8058HexaneHCID 5209483-Fluoro-4-nitrophenolHCID 820890Methyl 4-Chloropicolinate

Product 1

HCID 23153479HCID 23153479, compoundYield 27.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent3×

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 4-chloropyridine-2-carboxylate (200 mg), 3-fluoro-4-nitrophenol (202 mg) and chlorobenzene (0.6 ml) was stirred under a nitrogen atmosphere at 120° C. for 2 hrs and 20 min. The reaction mixture was cooled down to room temperature to give a solidified reaction mixture, which was then dissolved in a small amount of N,N-dimethylformamide and subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=1:2, ethyl acetate, then ethyl acetate:methanol=20:1 to 10:1). Fractions containing the target compound were concentrated to provide the titled compound (94 mg, 27.5%) as a pale yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. customto give
  3. customa solidified reaction mixture, which
  4. additionFractions containing the target compound
  5. concentrationwere concentrated

Sources & evidence

ORD record
ord-75602f149cd54316bf54fd3bc8881074
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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