Acetic Acid → 4-(6,7-Dimethoxyquinazolin-4-yloxy)benzene-1,2-diamine

Participants

Reaction Steps

4-(6,7-Dimethoxyquinazolin-4-yloxy)-2-nitro-phenylamine (Step A, 1 g, 2.9 mmol) was dissolved in EtOH (200 mL) and glacial acetic acid (10 mL) and placed under nitrogen. Pd/C was added, the reaction mixture blanketed with H2, the mixture was shaken under H2 for 18 h at 55 psi. The catalyst was removed by filtration through Celite® and the solution was concentrated in vacuo. The residue was dissolved in MeOH/H2O and NH4OH was added to adjust to PH 10, and the solvent evaporated. Purification of the residue by column chromatography using a gradient of 0-100% of a 90:10:1 (CH2Cl2:MeOH: NH4OH) afforded the title compound as a orange solid. MS(MH+)=N/A; Calc'd 312.32 for C16H16N4O3.

Provenance & Evidence