Acetic Acid → 2-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one

Participants

Role	Name	HCID	Charge
Reactant	Acetic Acid	HCID 176	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	Methyl 2-formyl-6-nitrobenzoate	HCID 346007	—
Reactant	4-Tert-butylphenylhydrazine hydrochloride	HCID 16217458	—
Solvent	Hexane	HCID 8058	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-(4-tert-butyl-phenyl)-8-nitro-2H-phthalazin-1-one	HCID 69158867	—

Reaction Conditions

Temperature	200 °C

Reaction Steps

A solution of the aldehyde (Step C, 0.58 g, 3.3 mmol), 4-t-butylphenylhydrazine-HCl (0.66 g, 3.3 mmol), AcOH (1 mL), and dioxane (3 mL) in a sealed reaction vial was heated at 200° C. for 20 min in a microwave. Upon cooling, the residue was diluted with EtOAc (10 mL), then hexane (10 mL). The resulting precipitate was filtered to afford the desired compound as a tan solid. MS m/e 324 (M+H)+. Calc'd for C18H17N3O3-323.35.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07390820B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-54fbdaa401e24893ab3ede98b6b1979f
Source note	uspto-grants-2008_06