1,2-Dichloroethane → HCID 58307476, compound

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Reaction Steps

Trifluoroacetic acid (100 uL, 1 mmol) in 1,2-dichloroethane (200 uL, 2 mmol) was added to 2-methyl-6-oxo-1-phenyl-4-trifluoromethyl-1,6-dihydro-pyridine-3-carboxylic acid tert-butyl ester (50 mg, 0.1 mmol). The obtained solution was stirred at r.t. overnight and evaporated. The residue was partitioned between 2M NaOH (4 mL) ethyl acetate (2×2 mL) to remove traces of the unreacted ester. The aqueous phase was acidified and the product extracted with ethyl acetate (2×3 mL). The combined organic solution was washed with brine, dried (MgSO4) and evaporated, yield 19.4 mg, 50%. LC-MS (m/z) 298.4 (MH+); tR=0.80 (method C).). 1H NMR (500 MHz, DMSO-d6): 1.99 (s, 3H, Me), 3.56 (br., CO2H+H2O), 6.86 (s, 1H, C5-H), 7.36 (d, J=7.3 Hz, 2H, two ortho-H of Ph), 7.50 (t, J=7.4 Hz, 1H, para-H of Ph), 7.56 (t, J=7.5 Hz, 2H, two meta-H of Ph).

Provenance & Evidence