Ammonia → 2,6-Dimethyl-4-(2-phenylethyl)pyridine

HRID 365695

Reaktionsgleichung

Reaktionsgleichung von HRID 365695
N.[NH2-].[Na+].[Na].[N:5]1[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[CH:7][C:6]=1[CH3:13].[CH2:14](Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[Cl-].[NH4+]>C(OCC)C.O.[N+]([O-])([O-])=O.[Fe+2].[N+]([O-])([O-])=O>[CH3:13][C:6]1[CH:7]=[C:8]([CH2:12][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:9]=[C:10]([CH3:11])[N:5]=1

Komponenten

10

Edukt 6

HCID 222AmmoniaHCID 7503Benzyl ChlorideHCID 79532,4,6-TrimethylpyridineHCID 24533Sodium amide2×HCID 25517Ammonium ChlorideHCID 5360545Sodium

Produkt 1

HCID 127330672,6-Dimethyl-4-(2-phenylethyl)pyridine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9815404Ferrous nitrateKatalysatorHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Liquid ammonia (150 ml) was introduced into a 250 ml three-necked round bottomed flask equipped with a mechanical stirrer, dropping funnel and outlet tube and immersed in a dry ice/ethanol bath. Sodium amide was generated by addition of 20 mg of iron nitrate (Fe3+) followed by metallic sodium (2.09 g, 0.09 mol). The deep blue solution was stirred for one hour and a solution of collidine (1) (10.06 g, 0.083 mol) in 20 ml of dry diethylether was introduced into the reaction by addition over a period of 15 min. The resultant yellow suspension was stirred for an additional 45 min, followed by the addition or benzylchloride (6.33 g, 0.05 mol) dissolvedin 10 ml of dry diethylether. The reaction mixture was stirred for 45 min and excess sodium amide was neutralized by addition of ammonium chloride (4.82 g, 0.09 mol) dissolved in 20 ml of H2O. Ammonia was evaporated and the residue was partitioned between water and diethylether. The collected etheral phase was dried over sodium sulfate and evaporated. The brown residual oil was fractionated, and a fraction distilling at 130° C./0.1 mmHg was colelcted.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. customimmersed in a dry ice/ethanol bath
  3. stirringThe resultant yellow suspension was stirred for an additional 45 min
  4. stirringThe reaction mixture was stirred for 45 min
  5. customAmmonia was evaporated
  6. customthe residue was partitioned between water and diethylether
  7. dry with materialThe collected etheral phase was dried over sodium sulfate
  8. customevaporated
  9. distillationa fraction distilling at 130° C./0.1 mmHg

Quellen und Nachweise

ORD-Eintrag
ord-18373e60d1af4e0fa4227e2b8c350b5d
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127529

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