Sodium Nitrite → 6-Nitro-1-phenyl-1,2-dihydroindazol-3-one

Participants

Reaction Conditions

Reaction Steps

Into a 1000-mL 4-necked round-bottom flask, was placed a solution of 2-amino-4-nitro-N-phenylbenzohydrazide (23 g, 84.56 mmol, 1.00 equiv) in ethanol (250 mL), 1N hydrogen chloride (250 mL), tetrahydrofuran (100 mL). To the resulting mixture was then added a solution of NaNO2 (17.5 g, 253.62 mmol, 3.00 equiv) in water (45 mL) dropwise with stirring at 72° C. in 40 min. The resulting solution was heated to reflux for 1 hr. The resulting mixture was then cooled to 25° C. The solids were collected by filtration to yield 6-nitro-1-phenyl-1,2-dihydroindazol-3-one as a brown solid. MS: 256 (MH+).

Provenance & Evidence