2,3,5-Trimethylpyridine → 2,3,5-Trimethyl-1-oxidopyridin-1-ium

HRID 1842401Notes

Reaction equation

HRID 1842401 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N:14]=1>C(Cl)Cl>[CH3:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][N+:14]=1[O-:9]

Participants

4

Reactant 2

HCID 127592,3,5-TrimethylpyridineHCID 70297m-Chloroperbenzoic acid

Product 1

HCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-iumYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloro per benzoic acid (10 g, 164.2 mmol) was added to a solution of 2,3,5-trimethylpyridine (10 g, 82.1 mmol) in DCM at 0° C. and the mixture was stirred at RT for 8 h (the reaction was monitored by TLC). The reaction was quenched with sodium bicarbonate solution and stirred for 1 h at RT. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 2,3,5-trimethylpyridine 1-oxide (6.5 g, 58.0%,) as a brown solid. 1H NMR: 200 MHz, CDCl3: δ 8.15 (s, 1H), 7.15 (s, 1H), 2.55 (s, 3H), 2.35 (s, 3H), 2.25 (s, 3H). MS: [M+H]+: m/z=311.2.

Workup

  1. customThe reaction was quenched with sodium bicarbonate solution
  2. stirringstirred for 1 h at RT
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-04ec0b7fa06744ed9ee9341d499e3464
Source dataset
uspto-grants-2015_02
Patent number
US08946222B2

Reaction notes

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