Ammonia → HCID 22147746, compound
Reaction equation
C([CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])#N.[NH3:13]>C(O)C.[Ni]>[NH2:13][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of the 2-cyanomethoxyanisole (5.6 g, 0.034 mol) in anhydrous ammonia (25 ml) and ethanol (50 ml) was heated to 120° C. at 500 psi for 12 h in the presence of raney nickel (1.4 g). The reaction mixture was filtered, concentrated under reduced pressure, the residue taken up in ether, and washed with 1.2 M HCl. The acidic phase was then rendered basic (pH=12) with careful addition of solid KOH and the alkaline solution extracted with ether. The organic phase was dried (MgSO4) and concentrated under reduced pressure to give the product (1.99 g, 35%) as an oil. IR. NMR. MS.
Workup
- filtrationThe reaction mixture was filtered
- concentrationconcentrated under reduced pressure
- washwashed with 1.2 M HCl
- additionwith careful addition of solid KOH
- extractionthe alkaline solution extracted with ether
- dry with materialThe organic phase was dried (MgSO4)
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-976374cd924e41e29fb2109e8a8d5f74
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07041684B2
Reaction notes
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