Methanol → 2-(Allyloxy)-4-aminobenzonitrile

HRID 474234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 474234
[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([N+:13]([O-])=O)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3].CO.[Cl-].[NH4+]>[Fe].O>[CH2:1]([O:4][C:5]1[CH:12]=[C:11]([NH2:13])[CH:10]=[CH:9][C:6]=1[C:7]#[N:8])[CH:2]=[CH2:3]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 597543072-(Allyloxy)-4-nitrobenzonitrile

Produkt 1

HCID 597542362-(Allyloxy)-4-aminobenzonitrileAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Iron powder-325 mesh (5.7 g, 98.0 mmol) was taken in a round bottom flask charged with a mixture of 2-(allyloxy)-4-nitrobenzonitrile (4.0 g, 19.6 mmol), absolute methanol (40 mL), water (8 mL) and ammonium chloride (5.2 g, 98 mmol). A water-cooled reflux condenser was attached to the flask and the heterogeneous mixture was heated to 65° C. with vigorous stirring for 50 min. The reaction mixture was filtered, and washed with methanol. The solvent was removed in vacuo. EtOAc was added to the residue, and the solution was washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated to afford 2-(allyloxy)-4-aminobenzonitrile (3.2 g, 94% yield) as a light-brown solid. LC-MS (M+H)+=175.2 1H NMR (400 MHz, CDCl3) δ ppm 7.29 (d, 1H, J=8.4 Hz), 6.22 (dd, 1H, J=2.0, 8.4 Hz), 6.14 (s, 1H), 6.07-5.98 (m, 1H), 5.48 (dd, 1H, J=1.6, 3.2 Hz), 5.44 (dd, 1H, J=1.6, 3.2 Hz), 4.59 (d, 2H, J=1.6 Hz).

Aufarbeitung

  1. temperaturereflux condenser
  2. filtrationThe reaction mixture was filtered
  3. washwashed with methanol
  4. customThe solvent was removed in vacuo
  5. additionEtOAc was added to the residue
  6. washthe solution was washed with water and brine
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-945d4a9acd534b9284b05514d5aa63c8
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637523B2

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