Phosphorus oxychloride → 6-Chloro-2-methyl-3-nitropyridine

HRID 1693345ノート

反応式

HRID 1693345 の反応式
[CH3:1][C:2]1[NH:7][C:6](=O)[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH3:1])[N:7]=1

参加物

3

反応物 2

HCID 24813Phosphorus oxychlorideHCID 5430532-Hydroxy-6-methyl-5-nitropyridine

生成物 1

HCID 2531236-Chloro-2-methyl-3-nitropyridine

反応条件

温度
115 °C

実験手順

A suspension of 6-methyl-5-nitro-1H-pyridin-2-one (Preparation 2, 3.53 g, 22.9 mmol) in phosphorous oxychloride (20 mL) was heated to 115° C. (oil bath temperature) for 3 h then allowed to cool to rt. The phosphorous oxychloride was removed in vacuo and the residue poured into iced water (100 mL). The mixture was quenched by addition of saturated sodium bicarbonate solution, then the aqueous mixture was extracted with ethyl acetate (3×100 mL). The combined organics were washed with brine, dried (MgSO4), filtered and concentrated in vacuo to furnish the title compound as a brown solid. δH (CDCl3): 2.86 (3H, s), 7.36 (1H, d, 8.59 Hz), 8.27 (1H, d, 8.32 Hz).

後処理

  1. temperatureto cool to rt
  2. customThe phosphorous oxychloride was removed in vacuo
  3. additionthe residue poured into iced water (100 mL)
  4. customThe mixture was quenched by addition of saturated sodium bicarbonate solution
  5. extractionthe aqueous mixture was extracted with ethyl acetate (3×100 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4568232b2e7842e1a3ce532e7cb3cb96
出典データセット
uspto-grants-2012_04
特許番号
US08158622B2

反応ノート

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