Methyl iodide → Methyl 5-chloro-2-(methylamino)benzoate

HRID 1435749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1435749
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].IC.[C:15](=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:7][O:6][C:4](=[O:5])[C:3]1[CH:8]=[C:9]([Cl:12])[CH:10]=[CH:11][C:2]=1[NH:1][CH3:15]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 78878Methyl 2-amino-5-chlorobenzoate

Produkt 1

HCID 12369447Methyl 5-chloro-2-(methylamino)benzoateAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-amino-5-chlorobenzoate (1.0 g, 5.4 mmol), iodomethane (0.75 ml, 12.0 mmol), potassium carbonate (1.7 g, 12.4 mmol), and acetonitrile (20 ml) was stirred for 48 hours. The mixture was filtered through a pad of celite under suction and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica eluting with ethyl acetate-hexane (1:19) to provide 5-chloro-2-methylaminobenzoic acid methyl ester (137 mg, 13% yield) followed by 5-chloro-2-dimethylaminobenzoic acid methyl ester (809 mg, 70% yield).

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of celite under suction
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica eluting with ethyl acetate-hexane (1:19)

Quellen und Nachweise

ORD-Eintrag
ord-9648d1fd319c417fb1ec923d852da6ea
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618968B2

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