* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
EXAMPLE M 2-Benzyloxy-6-bromo-benzo[de]isoquinoline-1,3-dione O-Benzyl hydroxylamine hydrochloride (2.0 g, 12.5 mmol) and <strong>[21563-29-1]4-bromo-1,8-naphthalic anhydride</strong> (2.9 g, 10.5 mmol) were reacted in pyridine (50 mL) following the procedure of Example D to give 3.5 g of the title compound.
With triethylamine; In tetrahydrofuran; for 6h;Reflux;
To a mixture of isatoic anhydride (10 g, 61.3 mmol) and O-benzylhydroxylaminehydrochloride (11.74 g, 73.6 mmol) in anhyd THF(100 mL) was added Et3N (12.39 g, 122.6 mmol). The mixture was heated at reflux temperature for 6 h. After evaporation of the solvent, EtOAc (150 mL) was added to the residue followed by H2O (100 mL) with vigorous shaking. The organic layer was separated, dried over anhyd Na2SO4, and concentrated to give a crude residue. Purification by flash column chromatography (EtOAc-PE, 2:1) gave benzamide 1f.
To a solution of 36 (0.175 g, 0.68 mmol) in 2 mL of H20 was added O- benzylhydroxylamine hydrochloride (0.70 g, 4.38 mmol). The reaction mixture was stirred at 50 C and monitored by TLC and/or LC/MS. After 16 h, O- benzylhydroxylamine hydrochloride (0.30 g, 1.88 mmol) was added and the reaction mixture was stirred 50 C for an extra 24 h. After complete consumption of the starting material, the aqueous solution was extracted with AcOEt (3 x 5 mL). The combined organic layer were dried over Na2S04, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (CH2Cl2:MeOH = 95:5 to 90: 10 v/v) to give 41 (0.12 g, 0.33 mmol) in 49% yield. LCMS (ESI) Calcd for C17H2iN306 363.4, observed (M + 1) 364.3
6-amino-2-benzyloxy-1Hbenzo[de]isoquinoline-1,3(2H)-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
59.3%
With triethylamine; In ethanol; for 5h;Reflux;
O-benzylhydroxylamine hydrochloride (1.60 g, 10 mmol) was dissolved in 20 mL of absolute ethanol and <strong>[6492-86-0]4-amino-1,8-naphthalic anhydride</strong> (0.30 g, 1.4 mmol) and triethylamine (1.01 g, 10 mmol), refluxed for 5 hours, concentrated to 5 mL, filtered and filteredThe cake was washed with ether and dried to give a yellow powder, 0.26 g, 59.3%.No purification is required for the next step.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
For Research Only
120K+ Compounds
Competitive Price
1-2 Day Shipping
