4-Aminophenol → HCID 71736090, compound

Participants

Reaction Conditions

Reaction Steps

Compound 3a (590 mg, 3.2 mmol), K2CO3 (887 mg, 6.4 mmol), KI (106 mg, 0.66 mmol) were mixed in DMF (50 mL). 4-aminophenol (600 mg, 5.4 mmol) was added portionwise, the reaction mixture was heated and stirred at 80° C. for 18 hr. After cooling to room temperature, the solvent was evaporated and the residue was quenched with 100 mL water. The mixture was adjusted pH to ˜7 with diluted hydrochloric acid. The mixture was then extracted with EtOAc and the combined organic layer was washed with water and then brine and dried over Na2SO4. The solvent was evaporated and the residue was purified by silica gel column chromatography provide the compound 21 (570 mg, 1.9 mmol, 60% yield) as a pale solid. 1H NMR (CDCl3, 400 MHz) δ 7.39 (d, J=9.2 Hz, 2H), 7.26 (t, J=7.6 Hz, 2H), 6.68-6.87 (m, 5H), 4.10 (t, J=6.0 Hz, 2H), 3.72 (t, J=6.4 Hz, 2H), 3.49 (q, J=7.2, 2H), 2.16 (s, 3H), 1.21 (t, J=7.2 Hz, 3H); HRMS (ESI, positive) m/z calcd. for C18H23N2O2 [M+H]+: 299.17540, found: 299.17538.

Provenance & Evidence