Ammonium Chloride → 2,6-Dimethylquinolin-5-amine

HRID 2088470

Reaktionsgleichung

Reaktionsgleichung von HRID 2088470
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[N+:12]([O-])=O)[N:3]=1.[NH4+].[Cl-]>C(O)C.O.[Fe]>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH3:15])[C:8]=2[NH2:12])[N:3]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 7665652,6-Dimethyl-5-nitroquinoline

Produkt 1

HCID 50336872,6-Dimethylquinolin-5-amineAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dimethyl-5-nitro-quinoline (192 mg, 0.95 mmol) in ethanol (9.3 mL) and water (4.7 mL) were added iron powder (280 mg, 5.0 mmol) and NH4Cl 280 mg, 5.2 mmol). The mixture was heated at reflux for 2 h, then cooled filtered. The filtrate was concentrated under reduced pressure, and the aqueous residue was extracted with ethyl acetate. The combined extracts were washed with water and brine, dried over Na2SO4, filtered and concentrated to dryness under reduced pressure. Purification of the residue by flash column (hexane/ethyl acetate gradient) gave 2,6-dimethyl-quinolin-5-ylamine (120 mg, 73%).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. extractionthe aqueous residue was extracted with ethyl acetate
  7. washThe combined extracts were washed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure
  11. customPurification of the residue by flash column (hexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-cab1453c767c4b8e92c962c81c382901
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08435990B2

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