Hydrochloric Acid → HCID 69482803, compound

Participants

Reaction Steps

To a solution of ethyl 7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (40 mg, 0.117 mmol) in N,N-dimethylformamide was added lithium bis(trimethylsilyl)amide (234 μL, 1.0 M in tetrahydrofuran, 0.234 mmol) dropwise. 1-Chloro-3-iodopropane (50 μL, 0.468 mmol) was added dropwise and stirred 4 hours at room temperature. The reaction mixture was acidified with cold 1 N aqueous hydrochloric acid and extracted with toluene. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration provided ethyl 1-(3-chloropropyl)-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 8.53 (d, J=1.1 Hz, 1 H), 7.50 (s, 1 H), 7.18 (dd, J=8.6, 5.3 Hz, 2 H), 7.03 (t, J=8.6 Hz, 2 H), 4.50 (q, J=7.1 Hz, 2 H), 4.27 (t, J=7.6 Hz, 2 H), 4.13 (s, 2 H), 3.61 (t, J=5.9 Hz, 2 H), 2.09 (m, 2 H), 1.47 (t, J=7.3 Hz, 3 H); MS m/z 417 (M−H)−.

Provenance & Evidence