Hydrazine → HCID 135703158, compound

Participants

Reaction Steps

An aqueous hydrazine solution (83%, 10 ml) in ethanol (10 ml) was added carefully at 28° under a nitrogen atmosphere to a mixture of 6-methyl-5-nitroquinazoline-4-one (formula 16, prepared according to Example VI) (10.0 g, 490 m-mol) and palladium-one-charcoal (10%, 1.0 g) in ethanol (150 ml). The mixture was refluxed for 1 hour. Cooling of the mixture to room temperature yielded crystals which were dissolved in dimethyl formamide (150 ml) and separated from the catalyst by filtration. The filtrate was evaporated and the residue recrystallized from ethanol. This yielded 7.0 g (82%) of the formula 17 target compound in the form of light yellow crystals, m.p. 260°-261° (decomp.); ir (KBr): 3480, 3315 cm-1 (NH2); pmr (DMSO-d6): δ 2.13 (s, 3 CH3), 6.70 (d, 1, J=8.5 Hz, H7), 6.95 (m, 2, D2O-exchangeable NH2), 7.36 (d, 1, J=8.5 Hz, H8), 7.88 (s, 1, H2), 11.67 (m, 1, D2O-exchangeable NH); ms (70 eV): m/e 175 (100%, M+).

Provenance & Evidence