Pyridine → HCID 59129384, compound

Participants

Reaction Steps

To a solution of methyl 4-(2-amino-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (260 mg, 1.0 mmol) and pyridine (160 mg, 2.0 mol) in CH2Cl2(20 mL) was added butyryl chloride (140 mg, 1.3 mmol) at 0° C. The reaction mixture was warmed to room temperature and stirred for 3 h before the mixture was poured into ice-water. The organic layer was separated and the aqueous phase was extracted with CH2Cl2(30 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and evaporated under reduced pressure to obtain methyl 4-(2-butyramido-5-nitrophenyl)-2,2-dimethylbut-3-ynoate (150 mg, 45%), which was used directly in the next step. NMR (400 MHz, CDCl3) δ 8.79(brs, 1 H), 8.71(d, J=9.2 Hz, 1 H), 8.24(d, J=2.8 Hz, 1 H), 8.17(dd, J=2.8, 9.2 Hz, 1 H), 3.82(s, 3 H), 2.55(t, J=7.2 Hz, 2 H), 1.85-1.75 (m, 2 H), 1.63(s, 6 H), 1.06(t, J=6.8 Hz, 3 H).

Provenance & Evidence