Sulfuric Acid → Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

Participants

Role	Name	HCID	Charge
Reactant	Sulfuric Acid	HCID 1118	—
Reactant	Acetic Anhydride	HCID 7918	—
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	9,10-Anthracenedione, 1-bromo-4-(methylamino)-	HCID 31418	—
Solvent	Water	HCID 962	—
Product	Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-	HCID 80770	—

Reaction Steps

A 250 ml flask equipped with a mechanical stirrer was charged with 30 g (95 mmole) of 1-methylamino-4-bromoanthraquinone (purchased from Sandoz), 19.5 g (191 mmole) of acetic anhydride, and 0.23 g of 96% H2SO4. The sludgelike mixture was heated and stirred at 110° for 30 minutes. The reaction mixture was cooled to 0° and 50 ml of H2O was added. After stirring 1/2 hour, 55 ml of 30% NaOH was added and the entire mixture was then transferred to a pressure reactor for the following reaction. A TLC (EtOAc) showed only a single product in the reaction.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04382800
Source dataset	uspto-grants-1983_05
ORD ID	ord-fc26286999464e4ebc5dbaf52d22d110
Source note	uspto-grants-1983_05