6-Nitro-3,4-dihydroquinazolin-4-one → 6-Amino-3,4-dihydroquinazolin-4-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-nitroquinazolin-4(3H)-one (4.15 g, 21.7 mmol) and 10% Pd/C (0.3 g) in MeOH (25 mL) and THF (50 mL) was stirred under H2 (1 atm) at 40° C. for 18 h. The mixture was diluted with DMF (50 mL), stirred overnight under H2, then placed under an Ar atmosphere. After the addition of Pd/C (0.4 g), the mixture was placed under an H2 atmosphere and warmed to 50° C. and stirred for 4 h. The reaction mixture was filtered through Celite®, washed with warm DMF (75 mL) and the combined filtrates evaporated to yield 6-aminoquinazolin-4(3H)-one (3.10 g, 88% yield) as a yellow solid. MS (ESI) m/e (M+H+) 162.3

Provenance & Evidence