[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[NH:10][CH2:9][CH2:8][CH2:7]2.[Cl:12][CH2:13][C:14](Cl)=[O:15].C(N(CC)CC)C>C(Cl)Cl>[Cl:12][CH2:13][C:14]([N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[CH:3][C:2]=2[CH3:1])[CH2:7][CH2:8][CH2:9]1)=[O:15]To a solution of 8-methyl-1,2,3,4-tetrahydroquinolin (1) (8.0 g, 54.3 mmol) in dry CH2Cl2 (250 mL) at 0° C. was added chloroacetyl chloride (4.8 mL, 60.3 mmol) followed by addition of triethylamine (8.4 mL, 60.3 mmol). The reaction mixture was stirred overnight under N2 and then diluted with CH2Cl2 (300 mL), washed with 1M HCl (2×225 mL), H2O (2×250 mL) and brine. Dried over Na2SO4, filtered and concentrated under reduce pressure to 12.67 g of crude material which was purified by column chromatography (EtOAc/Hexanes). Obtained 11.76 g (52.6 mmol) of target 2 (off-white solid) in 97% yield.
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