Nitrate → 2,6-Dimethyl-4-(2-(4-nitrophenyl)ethyl) pyridine

HRID 365696Notes

Reaction equation

HRID 365696 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:16])[N:3]=1.[N+:17]([O-])([OH:19])=[O:18].[N+]([O-])([O-])=O.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+]>C1COCC1.C(OCC)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:17]([O-:19])=[O:18])=[CH:12][CH:11]=2)[CH:5]=[C:4]([CH3:16])[N:3]=1

Participants

8

Reactant 5

HCID 943NitrateHCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 127330672,6-Dimethyl-4-(2-phenylethyl)pyridine

Product 1

HCID 178058592,6-Dimethyl-4-(2-(4-nitrophenyl)ethyl) pyridine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Compound (2) (20 g, 88.9 mmols) was dissolved in THF (150 ml), and nitric acid (6.7 ml, 60% aq. solution, 1 eq) was added. Diethylether was added to the clear solution until it remained turbid, and the mixture was left in the freezer for crystallization. The white crystals of nitrate (quantit. yield) were added in small portions to well-chilled sulfuric acid (150 ml), never allowing the temperature to reach 10° C., whereafter the mixture was warmed at 50° C. for 10 min. The resulting brown solution was poured onto ice and neutralized with solid sodium hydrogen carbonate. The organic material was extracted with chloroform (3×200 ml), and after drying over sodium sulphate, the chloroform extract was flash chromatographed using 4% ethanol/chloroform as a solvent. The appropriate fractions were collected and evaporated yielding a pure yellow solid

Workup

  1. waitthe mixture was left in the freezer for crystallization
  2. customto reach 10° C., whereafter the mixture
  3. extractionThe organic material was extracted with chloroform (3×200 ml)
  4. dry with materialafter drying over sodium sulphate
  5. extractionthe chloroform extract
  6. customchromatographed
  7. customThe appropriate fractions were collected
  8. customevaporated
  9. customyielding a pure yellow solid

Sources & evidence

ORD record
ord-aca7ace8c2f64f83bc14f077969c1cab
Source dataset
uspto-grants-2000_10
Patent number
US06127529

Reaction notes

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