Ethanol → 4-[(3,4-Dichloro-6-fluorophenyl)amino]-6-aminoquinazoline

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-nitroquinazoline (709 mg, 2.076 mmol) in 140 ml of 1:9:10 water:ethanol:iso-propylalcohol was heated to reflux temperature (95° C.). Additional 60 ml of the solvents mixture was added until complete dissolution. The reaction mixture was then cooled to 65° C., and 200 μl hydrazine hydrate (4.12 mmol) and 0.5 ml Raney®Nickel (in water) were added subsequently thereto. The resulting mixture was heated up to 80–85° C., additional 0.5 ml Raney®Nickel and 50 μl of hydrazine hydrate (1.03 mmol) were added, and gentle reflux was maintained for about 15–20 minutes. Filtration and evaporation gave 4-[(3,4-dichloro-6-fluorophenyl)amino]-6-aminoquinazoline (compound 2) in 83% yield. m.p.=265° C.; MS (m/z): 323.4, 325.4 (M+); Anal. calcd.: C, 52.9; H, 2.78; N, 17.33. Found: C, 52.19; H, 2.99; N, 17.14. HPLC analysis. C-18 column, 55% acetate buffer, PH=3.8/45% acetonitrile, flow=1 ml/min; r.t=6.6 minutes.

Provenance & Evidence