Hydrochloric Acid → 4-Ethoxy-2,5-dimethylpyridine 1-oxide

HRID 979871ノート

反応式

HRID 979871 の反応式
[Na].[CH3:2][C:3]1[CH:8]=[C:7]([N+]([O-])=O)[C:6]([CH3:12])=[CH:5][N+:4]=1[O-:13].Cl.[CH2:15]([OH:17])[CH3:16]>C(OCC)(=O)C>[CH2:15]([O:17][C:7]1[C:6]([CH3:12])=[CH:5][N+:4]([O-:13])=[C:3]([CH3:2])[CH:8]=1)[CH3:16]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 146707Pyridine, 2,5-dimethyl-4-nitro-, 1-oxideHCID 5360545Sodium

生成物 1

HCID 221514414-Ethoxy-2,5-dimethylpyridine 1-oxide

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

13.5 g of sodium were dissolved in 2300 ml of ethanol under argon. 60 g of 2,5-dimethyl-4-nitropyridine 1-oxide were then added portionwise thereto and the solution was left to boil under reflux overnight. The pH was adjusted to 7 with 5N hydrogen chloride in ethyl acetate while cooling, whereupon the mixture was evaporated in vacuo. The residue was taken up in 1 l of methylene chloride, the solution was filtered through silica gel, which was rinsed with 500 ml of methylene chloride, and the combined filtrates were evaporated in vacuo. The product was chromatographed on 300 g of silica gel with methylene chloride/methanol (95:5). After crystallization from ether/petroleum ether there was obtained 4-ethoxy-2,5-dimethylpyridine 1-oxide of melting point 65°-67°.

後処理

  1. waitthe solution was left
  2. temperatureunder reflux overnight
  3. temperaturewhile cooling, whereupon the mixture
  4. customwas evaporated in vacuo
  5. filtrationthe solution was filtered through silica gel, which
  6. washwas rinsed with 500 ml of methylene chloride
  7. customthe combined filtrates were evaporated in vacuo
  8. customThe product was chromatographed on 300 g of silica gel with methylene chloride/methanol (95:5)
  9. customAfter crystallization from ether/petroleum ether there

出典と根拠

ORDレコード
ord-88ad5636694a4587b51445e999459c58
出典データセット
uspto-grants-1987_01
特許番号
US04634710

反応ノート

読み込み中…