Nitric Acid → 4-Nitro-2,3,5-trimethylpyridine, 1-oxide

HRID 35468

反応式

HRID 35468 の反応式
[N+:1]([O-:4])(O)=[O:2].[CH3:5][C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][N+:7]=1[O-:14].[OH-].[Na+]>S(=O)(=O)(O)O>[CH3:5][C:6]1[C:11]([CH3:12])=[C:10]([N+:1]([O-:4])=[O:2])[C:9]([CH3:13])=[CH:8][N+:7]=1[O-:14]

参加物

5

反応物 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-ium

生成物 1

HCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxide

試薬・触媒・溶媒 1

HCID 1118Sulfuric Acid溶媒

実験手順

65 ml of fuming nitric acid (d =1.5) are added dropwise to 210 ml of conc. sulphuric acid while cooling. 96.5 g of 2,3,5-trimethylpyridine 1-oxide are subsequently added portionwise at 0°-5°, whereupon the mixture is stirred at room temperature for 1 hour, then heated to 90° within 3 hours and left at this temperature overnight. After cooling the solution is poured on to 1.5 kg of ice, whereupon the mixture is adjusted to pH 3 with conc. sodium hydroxide solution and extracted three times with 500 ml of methylene chloride. The combined organic phases are washed with 1 1 of water, dried over sodium sulphate and evaporated in vacuo. The residue is crystallized from ether/petroleum ether and there is obtained 2,3,5-trimethyl-4-nitropyridine 1-oxide of melting point 76°-78°.

後処理

  1. temperaturewhile cooling
  2. temperatureheated to 90° within 3 hours
  3. waitleft at this temperature overnight
  4. temperatureAfter cooling the solution
  5. extractionextracted three times with 500 ml of methylene chloride
  6. washThe combined organic phases are washed with 1 1 of water
  7. dry with materialdried over sodium sulphate
  8. customevaporated in vacuo
  9. customThe residue is crystallized from ether/petroleum ether

出典と根拠

ORDレコード
ord-8696c6546cb4490a8cc107f0fb9d9507
出典データセット
uspto-grants-1988_08
特許番号
US04766133

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