Hydrogen Bromide → HCID 178422725, compound

HRID 657660Notes

Reaction equation

HRID 657660 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([O-:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:5][CH:4]=1.Br.C(N(CC)CC)C.ClC1C=CC=C(C(OO)=O)C=1>CO.C(OCC)(=O)C.O>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][N+:12]([O-:15])=[C:11]([CH3:16])[CH:10]=2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 260Hydrogen BromideHCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 576720274-(4-Methoxyphenyl)-2-methylpyridine 1-oxide

Product 1

HCID 178422725HCID 178422725, compoundYield 15.3%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-(4-methoxyphenyl)-2-methylpyridine 1-oxide (384 mg) in a 48% aqueous solution of hydrobromic acid (2.08 mL) is heated under reflux for 4 hours. The mixture is allowed to cool back to room temperature, water and ethyl acetate are added and the two phases separated by decantation. The aqueous phase is concentrated under reduced pressure. The residue is dissolved in chloroform (4 mL); triethylamine (1 equivalent) is added followed by metachloroperbenzoic acid (1 equivalent). The mixture is stirred for two hours at room temperature; a few drops of methanol are added to dissolve the reactants and stirred again for one hour at room temperature. Concentration under reduced pressure affords 55 mg of 4-(4-hydroxyphenyl)-2-methylpyridine 1-oxide as a yellow oil used without further purification.

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe two phases separated by decantation
  3. concentrationThe aqueous phase is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in chloroform (4 mL)
  5. dissolutionto dissolve the reactants
  6. stirringstirred again for one hour at room temperature
  7. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-b9f5b596e64a4c85aa51231c3c6a4799
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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