Phenylacetyl chloride → HCID 54286782, compound

Participants

Reaction Steps

Dry CH2Cl2 (20 mL) was added to methyl 3-aminopicolinate (116) (0.421 g, 2.77 mmol). The solution was purged with nitrogen. Triethyl amine (1.16 mL, d=0.726, 8.31 mmol) was added to the solution via syringe. Phenylacetyl chloride (117) (0.805 mL, d=1.169, 6.09 mmol) was added to the solution via syringe. The mixture was stirred overnight at room temperature under nitrogen. The mixture was then stirred at 40° C. for 6 h. More triethyl amine (0.50 mL, 3.6 mmol) was added and, an hour later, more phenylacetyl chloride (0.400 mL, 3.02 mmol) was added. The mixture was stirred an additional hour and allowed to cool to room temperature. The reaction was quenched with water (20 mL), and the aqueous layer removed. The organic layer washed with water (3×15 mL), and dried with MgSO4. Silica gel was added and the slurry rota-evaporated to dryness. The resulting silica was chromatographed on silica (40 g, Davisil, grade 643, mesh 200-450) and eluded with EtOAc-hexanes (2:1, 400 mL). The appropriate fractions were collected (Rf =0.35). The solvent was rota-evaporated to yield the title compound (118) as a yellow oil, which, upon drying, precipitated out as a yellow solid (0.4463 g, 59.6%); Rf =0.35. 1H NMR (CDCl3) δ3.78 (s, 2, benzyllic), 3.97 (s, 3, CH3O--), 7.38 (m, 6, phenyl & H-5), 8.39, (dd, J1 =0.6, J2 =3.9, 1, H-4), 9.10 (dd, J1 =8.4, J2 =8.3, 1, H-6), 10.96 (s, 1, NH); MS (m./z) 270 (M+, 35), 211 (35), 179 (85), 153 (40), 147 (65), 119 (40), 94, (40), 91 (100).

Provenance & Evidence