Methanol → 2-(Allyloxy)-4-aminobenzonitrile
Reaction equation
[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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
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).
Workup
- temperaturereflux condenser
- filtrationThe reaction mixture was filtered
- washwashed with methanol
- customThe solvent was removed in vacuo
- additionEtOAc was added to the residue
- washthe solution was washed with water and brine
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-945d4a9acd534b9284b05514d5aa63c8
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637523B2
Reaction notes
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