Oxalyl chloride → HCID 66677692, compound

Participants

Reaction Steps

4-Cyano-2-fluorobenzoic acid (ABCR, 1.65 g, 10 mmol) was dissolved in DCM (40 mL). DMF (8 μl) was added at RT followed by oxalyl chloride (0.98 mL, 11.6 mmol). Once the gas evolution has ceased, the reaction mixture was evaporated to dryness. The residue was then dissolved in DCM (10 mL) and beta-alanine ethyl ester hydrochloride (1.54 g, 10 mmol) was added followed by dropwise addition of N-ethyldiisopropylamine (3.40 mL, 20 mmol) over 10 minutes. The reaction mixture was then washed with water and a saturated aqueous solution of NaHCO3, dried with MgSO4 and evaporated in vaccuo affording the title compound (2.27 g, 86%) as a white powder. 1H NMR (DMSO-d6, 300 MHz) δ 8.67 (t, J=5.0 Hz, 1H), 7.97 (dd, J=10.0, 1.3 Hz, 1H), 7.79 (dd, J=7.9, 1.4 Hz, 1H), 7.71 (m, 1H), 4.08 (q, J=7.2 Hz, 2H), 3.49 (m, 2H), 2.57 (t, J=6.9 Hz, 2H), 1.19 (t, J=7.2 Hz, 3H). LC/MS (Method B): 263.2 (M−H)−. HPLC (Method A) Rt 2.68 min (Purity: 98.5%).

Provenance & Evidence