m-Chloroperbenzoic acid → 2,6-Dimethylquinaldine N-oxide

HRID 1062498Notes

Reaction equation

HRID 1062498 reaction equation
[CH3:1][C:2]1([CH3:13])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[NH:3]1.ClC1C=C(C=CC=1)C(OO)=[O:19]>ClCCCl>[CH3:1][C:2]1([CH3:13])[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:12])[CH:8]=2)[NH+:3]1[O-:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 134958102,6-Dimethylquinaldine

Product 1

HCID 865882432,6-Dimethylquinaldine N-oxide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

To a stirring solution of 2,6-Dimethylquinaldine (1) (5 g, 0.0318 mol) in 1,2 dichloroethane (130 ml) was added 3-CPBA (3-chloro-peroxybenzoic acid) (7.43 g of 72% activity, 0.0310 mol). The reaction was then heated to 40° C. for 24 hours. The completed reaction mixture was allowed to cool to room temperature, concentrated, and 10% K2CO3 and a minimal amount of ethyl acetate was to produce a two phase mixture. A precipitate then formed in both layers and was filtered, washed with water to remove traces of K2CO3 and dried to afford 4.67 g (85%). H1 NMR (CDCl3): δ 2.52_(s, 3H), 2.66 (s, 3H), 7.28-7.56 (m, 4H), 8.70-8.79 (m, 1H).

Workup

  1. customThe completed reaction mixture
  2. temperatureto cool to room temperature
  3. concentrationconcentrated
  4. customto produce a two phase mixture
  5. customA precipitate then formed in both layers
  6. filtrationwas filtered
  7. washwashed with water
  8. customto remove traces of K2CO3
  9. customdried
  10. customto afford 4.67 g (85%)

Sources & evidence

ORD record
ord-cdaa0e561c0449d8b87ecffa99834b21
Source dataset
uspto-grants-2005_11
Patent number
US06962690B2

Reaction notes

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