m-Chloroperbenzoic acid → HCID 14044046, compound

HRID 1592406Notes

Reaction equation

HRID 1592406 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:20]>C(Cl)Cl>[CH3:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:20]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 12673496HCID 12673496, compound

Product 1

HCID 14044046HCID 14044046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-methyl-3-phenoxy-pyridine (0.501 g, 2.70 mmol) (Butler, D E et al. J. Med. Chem 1981, 24, 346-350) in CH2Cl2 (2.7 mL) was added 3-chloroperoxybenzoic acid (0.698 g, 4.05 mmol) and the solution stirred at room temperature for 24 h. Reaction mixture was diluted with CH2Cl2 (30 mL) and the organic layer was washed with saturated aqueous NaHCO3 (2×30 mL), dried (MgSO4), and concentrated to give 2-methyl-3-phenoxy-pyridine 1-oxide as a brown oil, which was used without further purification. 1H NMR (CDCl3) δ 2.54 (s, 3H), 6.77 (d, 1H), 6.97-7.06 (m, 3H), 7.16-7.21 (m, 1H), 7.34-7.41 (m, 2H), 8.11 (m, 1H).

Workup

  1. customReaction mixture
  2. washthe organic layer was washed with saturated aqueous NaHCO3 (2×30 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-57c69ee5778547c387572cdde1b7781a
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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