m-Chloroperbenzoic acid → 2,4-dimethyl-3-chloromethylpyridine-N-oxide

HRID 1693

反応式

HRID 1693 の反応式
[CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N:3]=1.ClC1C=CC=C(C(OO)=[O:19])C=1>C(Cl)(Cl)Cl>[CH3:1][C:2]1[C:7]([CH2:8][Cl:9])=[C:6]([CH3:10])[CH:5]=[CH:4][N+:3]=1[O-:19]

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 196909773-(Chloromethyl)-2,4-dimethylpyridine

生成物 1

HCID 196909962,4-dimethyl-3-chloromethylpyridine-N-oxide

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). The organic phase was dried with MgSO4, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 98:2 CH2 Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure the give the desired 2,4-dimethyl-3-chloromethylpyridine-N-oxide.

後処理

  1. extractionThe solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL)
  2. dry with materialThe organic phase was dried with MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under reduced pressure
  5. customThe residue was chromatographed on silica gel
  6. washMeOH and eluted with same
  7. customthe solvent was removed under reduced pressure the

出典と根拠

ORDレコード
ord-bc2379efbe054eccaf35ae30843004da
出典データセット
uspto-grants-1998_03
特許番号
US05726172

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