Hydrochloric Acid → 6-(3-Tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamine

HRID 1894649Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894649
C(O)C.Cl.[C:5]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[C:18]([CH3:19])=[CH:17][C:16]([N+:20]([O-])=O)=[CH:15][N:14]=1)([CH3:8])([CH3:7])[CH3:6]>[Fe].O>[C:5]([C:9]1[CH:10]=[C:11]([CH:23]=[CH:24][CH:25]=1)[O:12][C:13]1[N:14]=[CH:15][C:16]([NH2:20])=[CH:17][C:18]=1[CH3:19])([CH3:8])([CH3:6])[CH3:7]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 581533632-(3-Tert-butyl-phenoxy)-3-methyl-5-nitro-pyridine

Produkt 1

HCID 550806946-(3-Tert-butyl-phenoxy)-5-methyl-pyridin-3-ylamineAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer, a thermometer and a reflux condenser is charged with ethanol (50 ml), water (5 ml), iron (1.43 g) and hydrochloric acid 37% (0.2 ml). The reaction mixture is heated at 50° C. 2-(3-tert-Butyl-phenoxy)-3-methyl-5-nitro-pyridine (2.26 g) was added portionwise. The mixture is heated at reflux for 3 hours. After cooling the mixture to 50° C. it is filtered through celite. The filtrate is poured into water (200 ml) and extracted with ethylacetate (2×50 ml). The combined organic layers are washed with brine (100 ml), dried over sodium sulfate, filtered and the solvent is removed in vacuo. Purification by flash chromatography over silica gel with hexane/ethyl acetate 1:1 (v:v) gives 1.10 g of the compound as a brownish solid (MP: 83-84° C.).

Aufarbeitung

  1. customA 100 ml two-necked round-bottomed flask equipped with a KPG-stirrer
  2. temperatureThe mixture is heated
  3. temperatureat reflux for 3 hours
  4. temperatureAfter cooling the mixture to 50° C. it
  5. filtrationis filtered through celite
  6. additionThe filtrate is poured into water (200 ml)
  7. extractionextracted with ethylacetate (2×50 ml)
  8. washThe combined organic layers are washed with brine (100 ml)
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customthe solvent is removed in vacuo
  12. customPurification by flash chromatography over silica gel with hexane/ethyl acetate 1:1 (v:v)

Quellen und Nachweise

ORD-Eintrag
ord-7131c86062094bf28b9c0102f94d4459
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513286B2

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