Methyl iodide → 3-Amino-2-methoxy-4-nitrobenzonitrile

HRID 501546Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501546
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6].[C:14]([O-])([O-])=O.[K+].[K+].IC>CN(C=O)C>[NH2:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[C:5]#[N:6]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 218754622-Amino-4-cyano-3-hydroxynitrobenzene

Produkt 1

HCID 597543533-Amino-2-methoxy-4-nitrobenzonitrileAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirring suspension of 11A (0.34 g, 1.86 mmol) and K2CO3 (0.283 g, 2.05 mmol) in DMF (3 mL) was added iodomethane (0.127 mL, 2.05 mmol). After the addition, the reaction mixture was stirred at rt for 16 h, then partitioned between H2O and CH2Cl2. The separated CH2Cl2 layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was chromatographed (silica gel) eluting with 5% to 40% EtOAc/hexane to yield the title compound (0.22 g) as a solid.

Aufarbeitung

  1. additionAfter the addition
  2. custompartitioned between H2O and CH2Cl2
  3. washThe separated CH2Cl2 layer was washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed (silica gel)
  8. washeluting with 5% to 40% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b586bcadc939446697011a3c4515621d
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772267B2

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