15462-91-6

Usage

Uses

Due to the limited information available on 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethylphenyl]pentan-2-one, its applications are not well-documented. However, given its structural features, it may have potential uses in various industries, such as:
Used in Pharmaceutical Industry:
3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethylphenyl]pentan-2-one could be used as an intermediate compound for the synthesis of pharmaceuticals, given its complex structure and functional groups. Its potential role in drug development could be due to its ability to interact with biological targets or serve as a building block for more complex molecules.
Used in Chemical Research:
In the field of organic chemistry, 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethylphenyl]pentan-2-one may be used as a subject of study for understanding the reactivity and properties of complex organic molecules. Its synthesis and reactions could provide insights into new chemical pathways and mechanisms.
Used in Material Science:
3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one might also find applications in the development of new materials, such as polymers or composites, where its unique structure could contribute to specific properties like thermal stability, chemical resistance, or other desirable characteristics.

InChI:InChI=1/C22H26O6/c1-7-15(13(2)23)16-11-20(27-5)21(28-6)12-17(16)22(24)14-8-9-18(25-3)19(10-14)26-4/h8-12,15H,7H2,1-6H3

Synthetic route

C24H34O6 → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With silica gel In dichloromethane; sulfuric acid for 2h;	93%

1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indane (4483-47-0) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With hydrogenchloride; dihydrogen peroxide; acetic acid; copper(II) oxide In water at 3 - 25℃; for 10h; Reagent/catalyst; Temperature;	88.2%

1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman (2029-86-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + 2-(3,4-dimethoxybenzoyl)-4,5-dimethoxypropiophenone (102719-50-6)

Conditions	Yield
With chromium(VI) oxide; sulfuric acid In water; acetone for 2h; Ambient temperature;	A 48% B 24%

{4,5-dimethoxy-2-[1-(2-methyl-[1,3]dioxolan-2-yl)propyl]phenyl}(3,4-dimethoxyphenyl)methanone → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With sulfuric acid In dichloromethane at 20℃; for 2h;	32%

diazomethane (186581-53-3, 908094-01-9) + 2-(1-ethyl-2-oxo-propyl)-5,4'-dihydroxy-4,3'-dimethoxy-benzophenone → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With methanol

1-ethyl-3-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2-methyl-indene (82005-37-6) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman (2029-86-9) + acetic acid (64-19-7) + chromium (VI)-oxide → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

5.6-dimethoxy-2t-methyl-1r-ethyl-3c-<3.4-dimethoxy-phenyl>-indan → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With chromium(VI) oxide; acetic acid

(+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan (4483-47-0, 15161-79-2, 22688-51-3, 22688-52-4, 22688-53-5, 62211-17-0) + acetic acid (64-19-7) + CrO3 (2 mol) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
at 15 - 20℃;

(+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan (4483-47-0, 15161-79-2, 22688-51-3, 22688-52-4, 22688-53-5, 62211-17-0) + acetic acid (64-19-7) + CrO3 (3.3 mol) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid (7249-36-7) + Veratric acid (93-07-2)

Conditions	Yield
at 15 - 20℃;

3,4-dimethoxy-benzaldehyde (120-14-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / HCl gas / dioxane / 1 h / Heating 2: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

3-(3,4-dimethoxyphenyl)pentan-2-one → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium borohydride 2: 92 percent / HCl gas / dioxane / 1 h / Heating 3: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

3-(3,4-dimethoxyphenyl)-2-pentanol (102728-10-9) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / HCl gas / dioxane / 1 h / Heating 2: 48 percent / chromium trioxide, 35percent H2SO4 / acetone; H2O / 2 h / Ambient temperature View Scheme

2-ethyl-1-(3,4-dimethoxyphenyl)butan-1,3-dione + 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
With cesium fluoride In acetonitrile at 60℃; for 10h;

2-methoxy-4-propenylphenol (97-54-1) → 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuric acid / methanol / 2 h / Reflux 2: sodium hydroxide / methanol 3: hydrogenchloride; dihydrogen peroxide; copper(II) oxide; acetic acid / water / 10 h / 3 - 25 °C View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + toluene-4-sulfonic acid hydrazide (1576-35-8) → 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-p-toluenesulphonylimine (98352-06-8)

Conditions	Yield
hydrogenchloride In ethanol for 0.333333h; Heating;	85%

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + benzoic acid hydrazide (613-94-5) → 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-benzoylimine (98352-07-9)

Conditions	Yield
hydrogenchloride In ethanol for 0.333333h; Heating;	63%

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → tofisopam (22345-47-7, 914303-48-3, 914303-49-4, 914303-50-7, 914303-51-8)

Conditions	Yield
With hydrazine hydrate In ethanol for 1h; Heating;	60%
Stage #1: 3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one With hydrogenchloride; hydrazine hydrate; acetic acid In methanol; water at 20 - 27℃; for 2h; Stage #2: With ammonium hydroxide In water for 1h;

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 2,3,6,7-tetramethoxy-9,10-anthraquinone (5629-55-0) + 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid (7249-36-7)

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + aq.-ethanolic NaOH → 1-ethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-[2]naphthol (15462-94-9)

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + nitric acid (7697-37-2) + acetic acid (64-19-7) → 10-acetyl-2,3,6,7-tetramethoxy-anthrone (740836-53-7)

Conditions	Yield
Erwaermen der mit Wasser verduennten Reaktionsloesung;

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) + mineral acid → 6.7-dimethoxy-3-methyl-4-ethyl-1-<3.4-dimethoxy-phenyl>-isochromenylium salts

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 3-acetyl-1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3H-2,3-benzodiazepine (90140-50-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 64 percent / 3 h / Heating View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 3-Acetyl-1-(3,4-dimethoxyphenyl)-5-ethyl-4,5-dihydro-7,8-dimethoxy-4-methylen-3H-2,3-benzodiazepin (54080-15-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 20 percent / 3 h / Heating View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3,4-dihydro-5H-2,3-benzodiazepine

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent / hydrazin hydrate 98percent / ethanol / 1 h / Heating 2: 82 percent / sodium borohydride / methanol / 2 h / Ambient temperature View Scheme

3-[2-(3,4-dimethoxybenzoyl)-4,5-dimethoxyphenyl]pentan-2-one (15462-91-6) → 2,3,6,7-tetramethoxy-9,10-anthraquinone (5629-55-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: acetic acid; nitric acid / und Erwaermen der mit Wasser versetzten Reaktionsloesung 2: acetic acid; nitric acid / 100 °C View Scheme

Upstream product

• 82005-37-6 1-ethyl-3-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2-methyl-indene 
• 2029-86-9 1-(3,4-dimethoxyphenyl)-6,7-dimethoxy-4-ethyl-3-methylisochroman 
• 64-19-7 acetic acid 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 866252-52-0 4,5-dimethoxy-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 4483-47-0 1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indane 
• 97-54-1 2-methoxy-4-propenylphenol 
• 102728-10-9 3-(3,4-dimethoxyphenyl)-2-pentanol 
• 4483-47-0 (+-)-1r-ethyl-3c-(3,4-dimethoxy-phenyl)-5,6-dimethoxy-2t-methyl-indan 
• 186581-53-3 diazomethane 

Downstream Products

• 1616-49-5 4-ethyl-3-methyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)isoquinoline 
• 114920-22-8 4-ethyl-1-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-3-methyl-isoquinoline-2-oxide 
• 54080-15-8 3-Acetyl-1-(3,4-dimethoxyphenyl)-5-ethyl-4,5-dihydro-7,8-dimethoxy-4-methylen-3H-2,3-benzodiazepin 
• 90140-50-4 3-acetyl-1-(3,4-dimethoxyphenyl)-7,8-dimethoxy-5-ethyl-4-methyl-3H-2,3-benzodiazepine 
• 98352-06-8 4-Ethyl-6,7-dimethoxy-1-(3,4-dimethoxyphenyl)-3-methylisoquinoline-N-p-toluenesulphonylimine 
• 22345-47-7 tofisopam 
• 15462-94-9 1-ethyl-4-(3,4-dimethoxy-phenyl)-6,7-dimethoxy-[2]naphthol 
• 5629-55-0 2,3,6,7-tetramethoxy-9,10-anthraquinone 
• 7249-36-7 2-(3,4-Dimethoxy-benzoyl)-4,5-dimethoxy-benzoic acid 

Relevant academic research and scientific papers

holds the non-rope to divide method for the preparation of intermediates

The invention relates to a preparation method of a tofisopam intermediate 3-[2-(3,4-dimethoxy benzoic acyl)-4,5-dimethoxyphenyl]-penta-2-ketone, and belongs to the technical field of pharmaceutical synthesis. The method comprises the following step: carrying out reaction on 1-(3,4-dimethoxy-phenyl)-3-ethyl-5,6-dimethoxy-2-methyl-indan as an initial material, copper compounds as catalysts, and hydrogen peroxide as an oxidant under an acid condition, so as to prepare the tofisopam intermediate 3-[2-(3,4-dimethoxy benzoic acyl)-4,5-dimethoxyphenyl]-penta-2-ketone. According to the preparation method, the content of heavy metals in the wastewater is greatly lowered, chromium compounds with carcinogenesis are avoided, the production capacity of tofisopam is released, and the environment is protected.

One-pot synthesis of 2,3-benzodiazepines from arynes and β-diketones

Novel one-pot synthesis of 2,3-benzodiazepines from aryne precursors was accomplished. Tofisopam, well-known anxiolytics, could be synthesized via C-C bond insertion of 4,5-dimethoxybenzyne with 2-ethyl-1-(3,4-dimethoxyphenyl)- butane-1,3-dione, followed by the reaction with hydrazine hydrate in a one-pot operation. This protocol is applicable to the synthesis of other biologically active 2,3-benzodiazepines, such as Girisopam and Nerisopam.

PROCESS FOR THE PREPARATION OF 3-[2-(3,4-DIMETHOXYBENZOYL)-4,5- DIMETHOXYPHENYL] -PENTAN-2-ONE

The invention relates to a new process for the preparation of 3-[2-(3,4-dimethoxybenzoyl)-4,5- dimethoxyphenyl]-pentan-2-one of the formula (I), starting from a compound of the general formula (II) and subjecting the thus-obtained compound of the general formula (IV) to hydrolysis. The compound of the formula (I) is a pharmaceutical intermediate, which can be used for the preparation of an anxiolytic, namely tofisopam (INN).

PROCESS FOR THE PREPARATION OF 3-[2-(3,4-DIMETHOXY-BENZOYL)-4,5-DIMETHOXY-PHENYL]-PENTAN-2-ONE

The invention relates to a process for the preparation of 3-[2-(3,4-dimethoxy-benzoyl)-4,5-dimethoxy-phenyl]-pentan-2-one of the Formula (I) starting from a compound of the general Formula (II) (wherein R1 and R2 each stands for C1-4-alkyl or together form C2-6-alkylene).