Nitric Acid → 3-[(4-Nitrophenyl)methyl]pyridine

HRID 1154705

反応式

HRID 1154705 の反応式
[CH2:1]([C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:14]([O-])([OH:16])=[O:15].[OH-].[Na+]>>[N+:14]([C:5]1[CH:4]=[CH:3][C:2]([CH2:1][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)=[CH:7][CH:6]=1)([O-:16])=[O:15]

参加物

4

反応物 3

HCID 944Nitric AcidHCID 121123-BenzylpyridineHCID 14798Sodium Hydroxide

生成物 1

HCID 133648603-[(4-Nitrophenyl)methyl]pyridine

実験手順

3-Benzylpyridine (13.52 g, 0.080 mole) and nitric acid (70%, 100 ml) are stirred at 50° C. for 6 hr. The solution is poured into ice-water (1500 ml). The mixture is made alkaline by the careful addition of 50% aqueous sodium hydroxide and then extracted 4 times with 300 ml of ether. The extracts are washed with brine, dried (MgSO4), filtered, and concentrated. The crude product is crystallized from acetone-hexane giving 5.67 g of 3-(4'-nitrobenzyl)pyridine. The filtrate is concentrated and the residue is chromatographed in two equal portions (4.66 g each) over two Merck size C Lobar columns. The columns are eluted with 50% ethyl acetate-hexane. A less polar product [1.83 g, 3-(2'-nitrobenzyl)pyridine], mixed fractions (1.67 g), and additional 3-(4'-nitrobenzyl)pyridine (2.55 g) after crystallization from acetone-hexane, total 7.92 g, 0.037 mole, 46%). Two recrystallizations from acetone-hexane gives the titled product as colorless needles, having a melting point of 87°-88° C.

後処理

  1. extractionextracted 4 times with 300 ml of ether
  2. washThe extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is crystallized from acetone-hexane giving 5.67 g of 3-(4'-nitrobenzyl)pyridine
  7. concentrationThe filtrate is concentrated
  8. customthe residue is chromatographed in two equal portions (4.66 g each) over two Merck size C Lobar columns
  9. washThe columns are eluted with 50% ethyl acetate-hexane
  10. additionA less polar product [1.83 g, 3-(2'-nitrobenzyl)pyridine], mixed fractions (1.67 g), and additional 3-(4'-nitrobenzyl)pyridine (2.55 g)
  11. customafter crystallization from acetone-hexane, total 7.92 g, 0.037 mole, 46%)
  12. customTwo recrystallizations from acetone-hexane

出典と根拠

ORDレコード
ord-91d2471f6a8c4c4a9ef50ede0e6e20bb
出典データセット
uspto-grants-1984_12
特許番号
US04490531

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