[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][NH2:11])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[CH:9][CH2:10][NH2:11])=[CH:6][CH:7]=1
To a solution of 3-(4-chloro-phenyl)-prop-2-ynylamine (2.5 g) in 50 mL of THF at room temperature was added a 1M solution of LiAlH4 in THF (30 mL) and the mixture was heated at reflux for 1 hr. It was cooled to room temperature, and to it was successively added 1.1 mL H2O, 1.1 mL of 15% aq. NaOH and 3.4 mL H2O. The precipitated solid was filtered off and the filtrate was concentrated and purified by chromatography to provide 1.45 g of 3-(4-chloro-phenyl)-allylamine. NMR (400 MHz, CDCl3) 7.26-7.21 (m, 4H), 6.42 (dt, J=16.0, 1.6 Hz, 1H), 6.29-6.22 (m, 1H), 3.44 (dd, J=5.6, 1.6 Hz, 2H)
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