4-Nitrophenol → HCID 13882891, compound

HRID 542127Notes

Reaction equation

HRID 542127 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7](Cl)[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=1.[CH:21]1[C:26]([N+:27]([O-:29])=[O:28])=[CH:25][CH:24]=[C:23]([OH:30])[CH:22]=1.C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C(C)C>[N+:27]([C:26]1[CH:21]=[CH:22][C:23]([O:30][C:7]2[CH:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[N:4]=[C:3]([C:2]([F:20])([F:19])[F:1])[C:8]=2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:24][CH:25]=1)([O-:29])=[O:28]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 138828774-Chloro-2,6-bis-trifluoromethyl-nicotinic acid ethyl ester

Product 1

HCID 13882891HCID 13882891, compoundYield 54.5%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of 7.0 g (0.022 mol) of product of Example 19, 3.03 g (0.022 mol) of p-nitrophenol and 3.31 g (0.024 mol) of K2CO3 in 75 ml of methyl isobutyl ketone was refluxed for 17 hours. The cooled reaction mixture was concentrated in vacuo. The residue was dissolved in ether, washed with H2O, dried (MgSO4) and concentrated in vacuo. The residue was recrystallized in hot hexane to give 5.09 g of tan solid. The solid was purified by HPLC using 3% ethyl acetate/cyclohexane as eluting solvent affording 3.88 g (41.6%) of product as a white solid; mp 111.5°-113.5° C.

Workup

  1. temperaturewas refluxed for 17 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo
  4. dissolutionThe residue was dissolved in ether
  5. washwashed with H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was recrystallized in hot hexane

Sources & evidence

ORD record
ord-370982278d204d4185e31ef1672a8f65
Source dataset
uspto-grants-1987_04
Patent number
US04655816

Reaction notes

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