Phosphorus oxychloride → Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate

HRID 2277615ノート

反応式

HRID 2277615 の反応式
[Cl:1][CH2:2][C:3]1[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=[CH:5][N+:4]=1[O-].O=P(Cl)(Cl)[Cl:16]>>[Cl:16][C:5]1[CH:6]=[CH:7][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:3]([CH2:2][Cl:1])[N:4]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 582166522-(Chloromethyl)-3-(methoxycarbonyl)pyridine 1-oxide

生成物 1

HCID 59525762Methyl 6-chloro-2-(chloromethyl)pyridine-3-carboxylate収率 78%

実験手順

The crude of 2-(chloromethyl)-3-(methoxycarbonyl)pyridine-1-oxide (20 g, 99.5 mmol) was added in small portion to POCl3 (200 g) at room temperature. The mixture was refluxed for 3 hours before it was concentrated in vacuo. The residue was poured into ice-water, neutralized with NaHCO3 solution, and extracted with AcOEt (125 mL×3). The combined organic layers were concentrated to give the crude title product (17 g, yield 78%), which was used in the next step reaction without further purification.

後処理

  1. temperatureThe mixture was refluxed for 3 hours before it
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was poured into ice-water
  4. extractionextracted with AcOEt (125 mL×3)
  5. concentrationThe combined organic layers were concentrated

出典と根拠

ORDレコード
ord-27a3d3ed51754f22a14f0111ae4470b3
出典データセット
uspto-grants-2015_09
特許番号
US09133158B2

反応ノート

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