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

HRID 851070

Reaction equation

HRID 851070 reaction equation
[CH3:1][NH:2][C:3]1C2C(=O)[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8](=[O:18])[C:7]=2[C:6]([Br:19])=[CH:5][CH:4]=1.C(O[C:24](=[O:26])[CH3:25])(=O)C.OS(O)(=O)=O.[OH-].[Na+].[CH3:34][CH2:35][O:36]C(C)=O>O>[C:35]([N:2]([CH3:1])[C:3]1[C:25]2[C:24](=[O:26])[C:10]3[C:9](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:8](=[O:18])[C:7]=2[C:6]([Br:19])=[CH:5][CH:4]=1)(=[O:36])[CH3:34]

Participants

7

Reactant 5

HCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 314189,10-Anthracenedione, 1-bromo-4-(methylamino)-

Product 1

HCID 80770Acetamide, N-(4-bromo-9,10-dihydro-9,10-dioxo-1-anthracenyl)-N-methyl-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  1. customA 250 ml flask equipped with a mechanical stirrer
  2. temperatureThe sludgelike mixture was heated
  3. temperatureThe reaction mixture was cooled to 0°
  4. stirringAfter stirring 1/2 hour
  5. customthe entire mixture was then transferred to a pressure reactor for the following reaction
  6. customin the reaction

Sources & evidence

ORD record
ord-fc26286999464e4ebc5dbaf52d22d110
Source dataset
uspto-grants-1983_05
Patent number
US04382800

Linked notes

Loading…