2-Chloro-6-methylaniline → 1-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propane

HRID 1250890

Reaktionsgleichung

Reaktionsgleichung von HRID 1250890
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][OH:14]>>[Cl:1][C:2]1[C:7]([NH:8][CH2:11][CH2:12][CH2:13][OH:14])=[C:6]([CH3:9])[CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 2

HCID 68972-Chloro-6-methylanilineHCID 123083-Bromo-1-propanol

Produkt 1

HCID 183248341-(6-Chloro-2-methyl-phenyl)amino-3-hydroxy-propaneAusbeute 77,5 %

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of the 6-chloro-2-methyl aniline (70.8 g) and 3-bromo-1-propanol (27.8 g) was heated under nitrogen to 100° C. for 2 hours. The mixture was cooled and partitioned between dichloromethane and 1N sodium hydroxide. The organic layer was washed with 20% aqueous sodium chloride, dried over anhydrous potassium carbonate and evaporated to dryness. The residue was flash chromatographed on Merck-60 flash silica gel. Elution with a hexane-ethyl acetate gradient (from 8:1 to 3:1) provided the title compound (30.86 g, 77.5%) as a pale yellow oil, which was used as such in the next step.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between dichloromethane and 1N sodium hydroxide
  3. washThe organic layer was washed with 20% aqueous sodium chloride
  4. dry with materialdried over anhydrous potassium carbonate
  5. customevaporated to dryness
  6. customchromatographed on Merck-60 flash silica gel
  7. washElution with a hexane-ethyl acetate gradient (from 8:1 to 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-6933b08cc7444a80b7fc9aa0589b3d27
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06340687B1

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