Pyridine → 2-Chloro-5-methyl-3-nitropyridine

HRID 72644ノート

反応式

HRID 72644 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](=O)[NH:6][CH:7]=1.N1C=CC=CC=1.P(Cl)(Cl)([Cl:20])=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[Cl:20][C:5]1[C:4]([N+:9]([O-:11])=[O:10])=[CH:3][C:2]([CH3:1])=[CH:7][N:6]=1

参加物

6

反応物 4

HCID 1049PyridineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 3456432-Hydroxy-5-methyl-3-nitropyridine

生成物 1

HCID 8183002-Chloro-5-methyl-3-nitropyridine収率 75.3%

試薬・触媒・溶媒 1

HCID 7964Chlorobenzene溶媒

実験手順

A solution of 5-methyl-3-nitro-1H-pyridone (3.1 g, 20 mmol) in 50 mL chlorobenzene was treated with pyridine (0.47 g, 6.0 mmol) and phosphorus oxychloride (4.7 g, 30.8 mmol). The mixture was refluxed for 1 h. Upon cooling it was treated with sodium carbonate aq. followed by extraction with CH2Cl2. The organic phase was dried over Mg2SO4 and filtered. The solvent was evaporated in vacuo to give 2.6 g of the titled compound which was further purified by flash chromatography on silica gel (PE:EtOAc, 8:2, v/v). 1H-NMR (CDCl3) δ: 2.45 (s, 3H, CH3), 8.44 (d, 1H, J=2.0 Hz, Py-H), 8.58 (d, 1H, J=2.0 Hz, Py-H); MS (ESI+) m/z 173.0209 [M+H]+, C6H5ClN2O2 requires 172.0040.

後処理

  1. temperatureThe mixture was refluxed for 1 h
  2. temperatureUpon cooling it
  3. extractionfollowed by extraction with CH2Cl2
  4. dry with materialThe organic phase was dried over Mg2SO4
  5. filtrationfiltered
  6. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-bc06ef7e8e45493bbceced2dbb99d141
出典データセット
uspto-grants-2014_09
特許番号
US08829003B2

反応ノート

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