Nitric Acid → 3-(4-Nitrophenyl)pyridine

HRID 1279930

反応式

HRID 1279930 の反応式
OS(O)(=O)=O.[C:6]1([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:18]([O-])([OH:20])=[O:19].[OH-].[Na+]>>[N+:18]([C:9]1[CH:8]=[CH:7][C:6]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[CH:11][CH:10]=1)([O-:20])=[O:19]

参加物

5

反応物 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 138863-PhenylpyridineHCID 14798Sodium Hydroxide

生成物 1

HCID 2315043-(4-Nitrophenyl)pyridine収率 99%

実験手順

To a solution of H2SO4 (6 mL) cooled in an ice bath to 0° C. was added 3-phenylpyridine (1.0 g, 6.4 mmol). The orange-red solution was vigorously stirred while HNO3 (1 mL) was slowly added dropwise to give a cloudy light yellow solution. After stirring at room temperature for 20 min the solution was carefully poured into a beaker filled with ice (200 g). The solution was neutralized with 20% NaOH to give a cloudy white suspension which was extracted with EtOAc (3×150 mL). The organic layers were combined, washed with brine (2×50 mL), dried (NaSO4) and concentrated in vacuo to give the desired product (1.2 g, 99%) as a light yellow solid. Data for 3-(4-nitrophenyl)pyridine: Rf=0.47 (silica gel, methanol/CHCl3, 5/95); 1H NMR (400 MHz, acetone-d6) 8.99 (s, 1H), 8.67 (s, 1H), 8.37 (d, J=7.0, 2H), 8.18 (m, 1H), 8.02 (d, J=7.0, 2H), 7.53 (m, 1H).

後処理

  1. additionwas slowly added dropwise
  2. customto give a cloudy light yellow solution
  3. additionwas carefully poured into a beaker
  4. customto give a cloudy white suspension which
  5. extractionwas extracted with EtOAc (3×150 mL)
  6. washwashed with brine (2×50 mL)
  7. dry with materialdried (NaSO4)
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-d4bbca6994cb403abbaf57748d7f9cfc
出典データセット
uspto-grants-2002_09
特許番号
US06448405B1

関連ノート

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