Potassium Phosphate, Dibasic → 6-Phenylpyridine-2-carboxylic acid N-oxide

HRID 347536Notes

Reaction equation

HRID 347536 reaction equation
[C:1]1([C:7]2[N:12]=[C:11]([C:13]([OH:15])=[O:14])[CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:16]P([O-])([O-])=O.[K+].[K+].C1C=C(Cl)C=C(C(OO)=O)C=1>ClC(Cl)C>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([C:13]([OH:15])=[O:14])[N+:12]=2[O-:16])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 70297m-Chloroperbenzoic acidHCID 27628846-Phenylpyridine-2-carboxylic Acid

Product 1

HCID 210815386-Phenylpyridine-2-carboxylic acid N-oxideYield 68.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6-phenylpicolinic acid (150 mg, 0.75 mmol), K2HPO4 (600 mg) m-CPBA (300 mg, max 70% from Aldrich) in dichloroethane (8.0 mL) was heated at 60° C. for 1.5 h. Additional m-CPBA (2×300 mg) was added and the mixture was heated at 60° C. for 40 min. The reaction mixture was purified by preparative HPLC to afford the desired product (110 mg, 68%) as a white solid. 1H NMR (DMF-d7) δ 8.57 (s, 1H), 8.43 (d, 1H, J=2.2 Hz), 8.10–7.88 (m, 5H), 7.59–7.57 (m, 3H).

Workup

  1. temperaturethe mixture was heated at 60° C. for 40 min
  2. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-084baaa9df2d4e2ea02ca410a20b672e
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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