Aluminium lithium hydride → 1-[(1-Aminopropan-2-YL)oxy]-2-methoxybenzene
Reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH:6]([CH3:9])[C:7]#[N:8].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[O:5][CH:6]([CH3:9])[CH2:7][NH2:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
To a solution of 2-(2-methoxy-phenoxy)-propionitrile (3.91 g, 0.022 mol) in anhydrous ethyl ether (30 ml) was added lithium aluminum hydride (1.0 M, 44 ml, 0.044 mol). The mixture was heated at 65° C. for 18 hours and the reaction was quenched with water (3 ml), 15% NaOH (3 ml) and water (9 ml). The resulting material was filtered through celite. The celite was washed with methanol (200 ml), and the solvent was removed under vacuum. Chromatography (10% methanol-methylene chloride) afforded 0.26 g (7%) of product as yellow oil. MS EI m/e 181 (M+).
Workup
- customthe reaction was quenched with water (3 ml), 15% NaOH (3 ml) and water (9 ml)
- filtrationThe resulting material was filtered through celite
- washThe celite was washed with methanol (200 ml)
- customthe solvent was removed under vacuum
Sources & evidence
- ORD record
- ord-38d91e679b8144c29a7846946780722e
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06121307
Reaction notes
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