Hydrochloric Acid → 2-Amino-4-chloro-5-methylphenol

HRID 337366

Reaktionsgleichung

Reaktionsgleichung von HRID 337366
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[C:4]([N+:10]([O-])=O)[CH:3]=1.Cl.[Cl-].[NH4+]>CO.O.[Zn]>[NH2:10][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([CH3:8])=[CH:6][C:5]=1[OH:9]

Komponenten

7

Edukt 3

HCID 313Hydrochloric AcidHCID 235324-Chloro-5-methyl-2-nitrophenolHCID 25517Ammonium Chloride

Produkt 1

HCID 1045242-Amino-4-chloro-5-methylphenolAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-5-methyl-2-nitrophenol (5.0 g) in methanol (100 mL) at 0° C. was added zinc powder (8.71 g), which was activated by hydrochloric acid in advance, and a solution of ammonium chloride (7.1 g) in water (20 mL). The suspension was stirred for 4 h at room temperature. Then the insoluble material was filtered off through celite, and the celite cake was washed with ethyl acetate (100 mL). The filtrate and washings were combined and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel using hexane/ethyl acetate (3:2) to yield the title compound (1.4 g).

Aufarbeitung

  1. filtrationThen the insoluble material was filtered off through celite
  2. washthe celite cake was washed with ethyl acetate (100 mL)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-97d8b1235d82491fa0de0d796401146c
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889727B2

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