Acetic Anhydride → 2-Chloro-3-nitro-6-acetoxymethylpyridine

HRID 864974ノート

反応式

HRID 864974 の反応式
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH3:11])[N+:3]=1[O-].[C:13]([O:16]C(=O)C)(=[O:15])[CH3:14]>>[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([CH2:11][O:16][C:13](=[O:15])[CH3:14])[N:3]=1

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 194174682-Chloro-3-nitro-6-picoline-N-oxide

生成物 1

HCID 194174532-Chloro-3-nitro-6-acetoxymethylpyridine

反応条件

温度
60 °C

実験手順

2-Chloro-3-nitro-6-picoline-N-oxide (1,6 g, 8.5 mmol) was dissolved in acetic anhydride (5 mL) and the solution was heated in a 60° C. oil bath for 3 hours. The solvents were removed under vacuum and the dark residue was partitioned between methylene chloride (30 mL) and saturated aqueous potassium carbonate (100 mL). The aqueous layer was re-extracted with more methylene chloride (2×40 mL) and the combined methylene chloride layers were dried with magnesium sulfate, filtered and evaporated under vacuum. The crude solid was dissolved in methylene chloride (SmL) and was loaded onto a silica gel column (E. Merck 60, 230-400 mesh, 2.5×24 cm). The column was eluted with methylene chloride collecting 8 mL fractions. Fractions 11-26 were combined and evaporated to give the title compound (0.42 g) as a white solid.

後処理

  1. customThe solvents were removed under vacuum
  2. customthe dark residue was partitioned between methylene chloride (30 mL) and saturated aqueous potassium carbonate (100 mL)
  3. extractionThe aqueous layer was re-extracted with more methylene chloride (2×40 mL)
  4. dry with materialthe combined methylene chloride layers were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under vacuum
  7. dissolutionThe crude solid was dissolved in methylene chloride (SmL)
  8. washThe column was eluted with methylene chloride collecting 8 mL fractions
  9. customevaporated

出典と根拠

ORDレコード
ord-410ce3bbfe464423adcedbfbc5a627d6
出典データセット
uspto-grants-1996_10
特許番号
US05565445

反応ノート

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