Hydrochloric Acid → 4-Amino-2-methoxybenzonitrile

HRID 1967231

Reaktionsgleichung

Reaktionsgleichung von HRID 1967231
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].Cl.C(=O)([O-])O.[Na+]>C(O)C.[Fe]>[NH2:11][C:9]1[CH:8]=[CH:7][C:4]([C:5]#[N:6])=[C:3]([O:2][CH3:1])[CH:10]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 2918672-Methoxy-4-nitrobenzonitrileHCID 516892Sodium Bicarbonate

Produkt 1

HCID 2327354-Amino-2-methoxybenzonitrileAusbeute 73,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Methoxy-4-nitrobenzonitrile (5.0 g) and iron powder (7.84 g) were suspended in ethanol (150 mL), and concentrated hydrochloric acid (35 mL) was added dropwise at room temperature. The reaction mixture was stirred at room temperature for 3 hr, neutralized with sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained solid was washed with hexane to give the title compound as a red-brown solid (yield: 3.05 g, 73%).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. washthe obtained solid was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-bbf035aa8a5044178761697efb16b4a2
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420694B2

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