3271-05-4

Usage

Uses

Used in Pharmaceutical Industry:
6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione is used as a pharmaceutical candidate for its potential therapeutic applications. Its unique structure and pharmacological properties make it a valuable target for drug development, with the aim of creating new treatments for various diseases and conditions.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, 6-methoxy-2-methyl-1H-benz[de]isoquinoline-1,3(2H)-dione serves as an interesting target for research. Its unique structure and potential pharmacological properties provide opportunities for the discovery of novel drug candidates and the advancement of our understanding of disease mechanisms and treatment strategies.

InChI:InChI=1/C14H11NO3/c1-15-13(16)9-5-3-4-8-11(18-2)7-6-10(12(8)9)14(15)17/h3-7H,1-2H3

Synthetic route

methanol (67-56-1) + 4-nitro-N-methyl-1,8-naphthalimide (39061-36-4) → 6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4)

Conditions	Yield
With potassium carbonate sonication;	97%

sodium methylate (124-41-4) + 4-chloro-N-methyl-1,8-naphthalimide (4118-33-6) → 6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4)

Conditions	Yield
copper(II) sulfate In methanol for 12h; Heating;	86%

4-bromo-N-methyl-1,8-naphthalimide (4116-90-9) + sodium methylate (124-41-4) → 6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4)

Conditions	Yield
With copper(ll) sulfate pentahydrate In methanol Reflux;	81%
With copper(ll) sulfate pentahydrate In methanol Reflux;

4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) → 6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / 8 h / 80 °C 2: copper(ll) sulfate pentahydrate / methanol / Reflux View Scheme
Multi-step reaction with 2 steps 1: ethanol / 55 °C 2: copper(ll) sulfate pentahydrate / methanol / Reflux View Scheme

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → 6-hydroxy-2-methyl-1H-benz[d,e]isoquinoline-1,3(2H)-dione (784-03-2)

Conditions	Yield
With hydrogen iodide for 3h; Heating;	81%
With pyridine hydrochloride at 190℃; for 0.583333h; demethylation;	45%
With hydrogen iodide In water at 130℃; Inert atmosphere;
With hydrogen iodide at 140℃;

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → 2,3,6-trimethylfuro<2,3-b><1>naphtho<4a,7a-e,f>pyrida-5,7-dione (146774-97-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 81 percent / 57percent HI / 3 h / Heating 2: K2CO3 / butan-2-one / 72 h / Heating 3: 53 percent / 98percent H2SO4 / 10 h / Ambient temperature View Scheme

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → 2-methyl-6-(2'-oxobutan-3'-yl)-naphtho<3a,9a-c,d>pyrida-1,3-dione (146774-96-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / 57percent HI / 3 h / Heating 2: K2CO3 / butan-2-one / 72 h / Heating View Scheme

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → 2-methyl-6-acetoxy-5-acetyl-naphtho<3a,9a-c,d>pyrida-1,3-dione (146774-98-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 81 percent / 57percent HI / 3 h / Heating 2: K2CO3 / butan-2-one / 72 h / Heating 3: 53 percent / 98percent H2SO4 / 10 h / Ambient temperature 4: 84 percent / O2, TPP / CH2Cl2 / 0.5 h / -10 °C / Irradiation View Scheme

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → 6-hydroxy-2-methyl-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5-carbaldehyde

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen iodide / water / 130 °C / Inert atmosphere 2.1: trifluoroacetic acid / 10 h / 0 - 120 °C 2.2: 2 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: hydrogen iodide / 140 °C 2.1: trifluoroacetic acid / 120 °C / Cooling with ice 2.2: Heating View Scheme

6-methoxy-2-methyl-1H-benzo[de]isoquinoline-1,3(2H)-dione (3271-05-4) → C20H12N2O3S

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen iodide / water / 130 °C / Inert atmosphere 2.1: trifluoroacetic acid / 10 h / 0 - 120 °C 2.2: 2 h / Reflux 3.1: dihydrogen peroxide; hydrogenchloride / ethanol; water / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: hydrogen iodide / 140 °C 2.1: trifluoroacetic acid / 120 °C / Cooling with ice 2.2: Heating 3.1: hydrogenchloride; dihydrogen peroxide / ethanol; water / 0.5 h / 20 °C View Scheme

Upstream product

• 81-86-7 4-bromo-1,8-naphthalenedicarboxylic anhydride 
• 4116-90-9 4-bromo-N-methyl-1,8-naphthalimide 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 
• 39061-36-4 4-nitro-N-methyl-1,8-naphthalimide 
• 4118-33-6 4-chloro-N-methyl-1,8-naphthalimide 

Downstream Products

• 784-03-2 6-hydroxy-2-methyl-1H-benz[d,e]isoquinoline-1,3(2H)-dione 

Relevant academic research and scientific papers

Synthesis and Photooxygenation of 2,3,6-Trimethylfuronaphthopyrida-5,7-dione, A Potential Chemiluminescent Probe for Singlet Oxygen

As potential chemiluminescent probe for singlet oxygen, the furonaphthalimide 4 was synthesized in five steps (ca. 25percent overall yield), by starting from commercially available 4-chloro-1,8-naphthalic anhydride; its photooxygenation at -10 deg C gave the cleavage product 6 of the intermediary dioxetane 5, which is thermally too labile for isolation and could not be detected even by low temperature NMR spectroscopy.The new 1,8-naphthalimide derivatives 3,4 and 6 were fully characterized and their absorption and fluorescence spectral properties were determined.

Solvent influence on the photophysical properties of 4-methoxy-N-methyl-1,8-naphthalimide

4-Methoxy-N-methyl-1,8-naphthalimide (1) exhibits considerable solvatochromism and its UV-vis spectral properties have been studied in several polar/non-polar and protic/aprotic solvents, as well as in ethanol-water mixtures. The results reveal a strong influence of the solvent's polarity and its hydrogen-bond donor (HBD) capability on the photophysical properties of 1. For binary ethnaol/water mixtures, preferential solvation models describe the band shifts in the probe's visible absorption spectrum well, but they fail to describe the correponding shifts of the emission maxima. Pseudolinear approximations between solvent composition and molecule's transition energies, ET, can be used to study the composition of ethanol-water mixtures, simplifying the mathematical treatment for eventual analytical applications.

Naphthalimide/benzimide-based excited-state intramolecular proton transfer active luminogens: Aggregation-induced enhanced emission and potential for chemical modification

Fluorescent organic particles are important in a number of areas, including medical imaging; hence, the development of organic materials that exhibit aggregation-induced emissions is an important objective. To that end, we report the synthesis of naphthalimide- and benzimide-based 2-(2-hydroxyphenyl)benzothiazole (HBT) derivatives (HNIBT and HPIBT, respectively) that exhibit aggregation-induced emission enhancement (AIEE), in contrast to most naphthalimide- or benzimide-based derivatives that are prone to aggregation-induced quenching. Experimental studies like single-crystal X-ray diffraction analysis and theoretical calculations demonstrate that the ability to undergo excited-state intramolecular proton transfer is pivotal for AIEE. Further studies revealed that a terminal alkynyl chain at the N-imide site of HPIBT has little impact on the emission behavior of the resultant compound (HPIBT-yl). HPIBT-Pe, an amphiphilic molecule obtained through the click reaction of HPIBT-yl and a tetraethylene-glycol-derived azide, self-assembled to form highly photostable particles that have long-term fluorescence imaging potential in cellular environments.

Synthesis method of aggregated state fluorescent enhancement dye for fluoride ion probe

The invention discloses a synthesis method of an aggregated state fluorescent enhancement dye based on a naphthalimide mother nucleus which can be used to design a fluoride ion probe, and belongs to the technical field of analytical chemistry. The high hydration energy of fluoride ion weakens the nucleophilicity, and the hydrophobic environment can enhance the nucleophilicity of fluoride ion, butmany fluorescent dyes show the aggregated state fluorescence quenching property in the hydrophobic environment. Through several steps, benzothiazole is introduced to the 2-position of 1-hydroxynaphthalimide, and the fluorescent dye with the aggregated state fluorescence enhancement characteristic is synthesized. The structure of the compound is characterized by NMR spectroscopy, the fluorescence spectra show that the excitation state proton transfer characteristic is the reason for the compound having the aggregated state fluorescence enhancement characteristic, the conclusion is supported bythe theoretical calculation, and thus the compound can be used to design the fluoride ion fluorescence probe with high sensitivity and selective specificity.