Methyl iodide → Benzamide, 2-hydroxy-6-methoxy-

HRID 1167349

Reaktionsgleichung

Reaktionsgleichung von HRID 1167349
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:3]=1[C:4]([NH2:6])=[O:5].[C:12](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.C(OCC)(=O)C.C(OCC)C>[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[C:3]=1[C:4]([NH2:6])=[O:5]

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 766022,6-Dihydroxybenzamide

Produkt 1

HCID 173610Benzamide, 2-hydroxy-6-methoxy-Ausbeute 69,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2,6-dihydroxybenzamide (2 g, 12.66 mmol) in dimethylformamide (100 mL) were added cesium carbonate (3.922 g, 12.03 mmol) and methyl iodide (756 μL, 12.03 mmol). The reaction mixture was stirred at room temperature for 36 h and was taken in 200 mL of ethyl acetate and diethyl ether (1:1 ratio). It was washed with water, brine and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 25% ethyl acetate in hexanes yielded 2-hydroxy-6-methoxy-benzamide (1.4 g, 66%).

Aufarbeitung

  1. washIt was washed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe solid was then filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  6. washeluting with 25% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5ecd000c1aea4027944e5d4c242af64e
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617346B1

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