13297-17-1

Basic information

• Product Name: 2-ACETYL-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE
• Synonyms: 2-ACETYL-3-METHYL-1,4-QUINOXALINEDIIUMDIOLATE;2-ACETYL-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE;AKOS BB-7528;1-(3-Methyl-1,4-dioxido-2-quinoxalinyl)ethanone;2-ACETYL-3-METHYLQUINOXALINEDIUM-1,4-DIOLATE;2-ACETYL-3-METHYLQUINOXALINE-1,4-DIOXIDE;2-Methyl-3-acetylquinoxaline-1,4-dioxide;2-Acetyl-3-methylquinoxaline 1,4-dioxide Solution, 100ppm
• CAS NO: 13297-17-1
• Molecular Formula: C₁₁H₁₀N₂O₃
• Molecular Weight: 218.21
• Mol File: 13297-17-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 153-154 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• PKA: 1.63±0.30(Predicted)
• CAS DataBase Reference: 2-ACETYL-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-ACETYL-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE(13297-17-1)
• EPA Substance Registry System: 2-ACETYL-3-METHYLQUINOXALINEDIIUM-1,4-DIOLATE(13297-17-1)

Safety Data

• Hazardous Substances Data: 13297-17-1(Hazardous Substances Data)

Usage

Uses

Mequindox is an intermediate in the synthesis of Desoxyquinocetone which is a metabolite of the veterinay drug Quinocetone.

InChI:InChI=1/C11H10N2O3/c1-7-11(8(2)14)13(16)10-6-4-3-5-9(10)12(7)15/h3-6H,1-2H3

Synthetic route

benzofurazan oxide (480-96-6) + acetylacetone (123-54-6) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
With triethylamine In ethanol at 45℃; for 2h;	94%
With triethylamine In ethanol for 3h; Ambient temperature;	86%
With silica gel for 0.0666667h; Microwave irradiation;	85%

[3H]-benzofurazan-N-oxide + acetylacetone (123-54-6) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
With ammonia In water; N,N-dimethyl-formamide at 25℃; for 16h; Temperature; Irradiation;	58.5%

benzofurazan oxide (480-96-6) + 2,5-hexanedione (110-13-4) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
Alkaline conditions;

C6H4N2O2*C42H70O35 (1322877-87-1) + acetylacetone (123-54-6) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
In methanol; water at 20℃;

2-nitro-aniline (88-74-4) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hypochlorite solution; potassium hydroxide / ethanol / 2.5 h / 20 °C 2.1: β‐cyclodextrin / methanol; water / 0.5 h 2.2: 0.33 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: potassium hydroxide / ethanol / Heating 1.2: 0.17 h / 0 °C 2.1: triethylamine / ethanol / 2 h / 45 °C View Scheme

benzofuroxane N-oxide (236092-93-6) + acetylacetone (123-54-6) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
With triethylamine

4-Bromo-2-nitroaniline (875-51-4) → 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium acetate / ethanol / 0.5 h / 30 °C / 600 Torr / Inert atmosphere 2: sodium hydroxide; sodium hypochlorite solution / isopropyl alcohol / 2 h / 35 °C 3: ammonia / N,N-dimethyl-formamide; water / 16 h / 25 °C / Irradiation View Scheme

benzaldehyde (100-52-7) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 1-(3-methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one (81810-66-4)

Conditions	Yield
With (2-hydroxyethyl)ammonium formate; calcium chloride In methanol at 50 - 65℃; for 3h; Concentration;	95%
With Acetate de N,N-dimethylamino-4 pyridinium In ethanol at 70℃; for 3h; Green chemistry;	95%
With magnesium sulfate; acetic acid In methanol; 2,2'-iminobis[ethanol] at 55℃; for 4h; Reagent/catalyst; Temperature;	94%

salicylaldehyde (90-02-8) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → (E)-3-methyl-2-(2'-hydroxyphenylethenecarbonyl)quinoxaline-1,4-dioxide

Conditions	Yield
With ammonium hydroxide In methanol at 36 - 45℃; for 8h;	94.7%

4-chlorobenzaldehyde (104-88-1) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(4-chlorophenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide (85108-69-6)

Conditions	Yield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;	90%
With sodium hydroxide In methanol at 5 - 10℃;	72%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

4-nitrobenzaldehdye (555-16-8) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-methyl-2-[3-(4-nitrophenyl)-2-propenoyl]quinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;	90%
With sodium hydroxide In methanol at 5 - 10℃;	42%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) + 3-Fluorobenzaldehyde (456-48-4) → (E)-2-(3-(3-fluorophenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol at 0℃;	90%

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-methyl-3-acetylquinoxaline (22059-64-9)

Conditions	Yield
With sodium dithionite In ethanol; water at 55 - 60℃;	88%
Stage #1: 3-methyl-2-acetylquinoxaline-1,4-dioxide In ethanol for 0.5h; Reflux; Stage #2: With sodium dithionite In ethanol for 2h; Reflux;	82%
With sulfur trioxide pyridine complex; sodium iodide In acetonitrile for 0.5h; Ambient temperature;	66%

benzaldehyde (100-52-7) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → (2E)-3-phenyl-1-(3-methyl-1,4-dioxyquinoxaline-2-yl)propenone (85108-59-4)

Conditions	Yield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;	85%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;	62%
With sodium hydroxide In methanol at 5 - 10℃;	62%
With sodium hydroxide In methanol at 0 - 5℃; for 0.666667h; Claisen-Schmidt Condensation;	10%

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 1-(3-methylquinoxalin-2-yl)ethan-1-ol (104217-24-5)

Conditions	Yield
With lithium aluminium tetrahydride; benzyltrimethylammonium chloride In tetrahydrofuran at 20℃; for 3h; Reagent/catalyst; Concentration;	84.9%

4-bromo-benzaldehyde (1122-91-4) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(4-bromophenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol for 0.166667h; Ambient temperature;	83%
With sodium hydroxide In methanol at 5 - 10℃;	54%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-Acetyl-3-Bromomethyl-Quinoxaline-1,4-Dioxide (60949-39-5)

Conditions	Yield
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane; chloroform for 24h; Heating;	81%
With bromine In methanol	71%
With bromine In methanol Ambient temperature;	70%
With bromine In methanol
With bromine In methanol

sodium 2-formylbenzenesulfonate (1008-72-6) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → C18H13N2O6S(1-)*Na(1+)

Conditions	Yield
With sodium carbonate In water at 10℃; for 3h; Temperature; Reagent/catalyst;	80%

sodium 4-carboxy-benzenesulfonate (13736-22-6) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → C18H13N2O6S(1-)*Na(1+)

Conditions	Yield
With sodium carbonate In water at 30℃; for 5h;	77.9%

piperonal (120-57-0) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(3,4-methylenedioxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	72%
With sodium hydroxide In methanol at -10℃; Claisen-Schmidt condensation;
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

4-methoxy-benzaldehyde (123-11-5) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(4-methoxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide (1172616-36-2)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	71%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-ethyl-3-methylquinoxaline (37920-99-3)

Conditions	Yield
With diphosphorus tetraiodide In chloroform for 5h; Ambient temperature;	70%

3,4-dichlorobenzaldehyde (6287-38-3) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → E-2-[3-(3,4-dichlorophenyl)-1-oxo-2-propenyl]-3-methylquinoxaline-1,4-dioxide (1172616-42-0)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	69%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;
Alkaline conditions;

3,4-dimethoxy-benzaldehyde (120-14-9) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(3,4-dimethoxyphenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide (1172616-37-3)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	68%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

3,4,5-trimethoxy-benzaldehyde (86-81-7) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-methyl-2-[3-(3,4,5-trimethoxyphenyl)-2-propenoyl]quinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	67%
With sodium hydroxide In methanol at -10℃; Claisen-Schmidt condensation;
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;
With sodium hydroxide In methanol at -10℃; Claisen-Schmidt Condensation;

4-fluorobenzaldehyde (459-57-4) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-[3-(4-fluorophenyl)-2-propenoyl]-3-methylquinoxaline-1,4-dioxide (1172616-46-4)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	66%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

3-Chlorobenzaldehyde (587-04-2) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-(3-(3-chlorophenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol at 0℃;	64.7%

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-bromoacetyl-3-methylquinoxaline-1,4-di-N-oxide

Conditions	Yield
With bromine; acetic acid at 20 - 60℃; for 10h;	62%

3-nitro-benzaldehyde (99-61-6) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-methyl-2-[3-(3-nitrophenyl)-2-propenoyl]quinoxaline-1,4-dioxide (85108-71-0)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	58%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

β-naphthaldehyde (66-99-9) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-methyl-2-[3-(naphth-2-yl)-prop-2-enoyl]quinoxaline 1,4-di-N-oxide (1443770-94-2)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; for 0.25h;	57%

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-Acetyl-2-methylquinoxaline 1-Oxide (61522-56-3) + 2-methyl-3-acetylquinoxaline (22059-64-9) + 2-Acetyl-3-methylquinoxaline 1-Oxide (61522-57-4)

Conditions	Yield
With xylene for 18h; Heating;	A 55.5% B 2.3% C 19.8%
With xylene for 18h; Heating; other 3-methylquinoxaline 1- and 4-oxide derivatives;	A 55.5% B 2.3% C 19.8%

3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-Acetyl-2-methylquinoxaline 1-Oxide (61522-56-3)

Conditions	Yield
With phosphorous acid trimethyl ester In isopropyl alcohol for 2h; Reflux;	48%
Multi-step reaction with 2 steps 1: 2.3 percent / xylene / 18 h / Heating; other 3-methylquinoxaline 1- and 4-oxide derivatives 2: 52.6 percent / hydrogen peroxide, sodium tungstate / acetic acid View Scheme

4-methyl-benzaldehyde (104-87-0) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 3-methyl-2-[3-(4-methylphenyl)-2-propenoyl]quinoxaline-1,4-dioxide (85108-70-9)

Conditions	Yield
With sodium hydroxide In methanol at 5 - 10℃;	46%
With sodium hydroxide In methanol; water at 5 - 10℃; for 0.0833333 - 0.166667h;

pyridine-4-carbaldehyde (872-85-5) + 3-methyl-2-acetylquinoxaline-1,4-dioxide (13297-17-1) → 2-methyl-3-(3-(pyridin-4-yl)acryloyl)quinoxaline-1,4-dioxide

Conditions	Yield
With sodium hydroxide In methanol at 0℃;	39.1%

Upstream product

• 123-54-6 acetylacetone 
• 875-51-4 4-Bromo-2-nitroaniline 
• 236092-93-6 benzofuroxane N-oxide 
• 88-74-4 2-nitro-aniline 
• 1322877-87-1 C₆H₄N₂O₂*C₄₂H₇₀O₃₅ 
• 480-96-6 benzofurazan oxide 
• 110-13-4 2,5-hexanedione 

Downstream Products

• 61522-56-3 3-Acetyl-2-methylquinoxaline 1-Oxide 
• 22059-64-9 2-methyl-3-acetylquinoxaline 
• 61522-57-4 2-Acetyl-3-methylquinoxaline 1-Oxide 
• 85108-59-4 (2E)-3-phenyl-1-(3-methyl-1,4-dioxyquinoxaline-2-yl)propenone 
• 174136-44-8 2-(3-(4-chlorophenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide 
• 174136-43-7 C₁₈H₁₃N₃O₅ 
• 81810-72-2 2-(3-(4-methoxyphenyl)acryloyl)-3-methylquinoxaline-1,4-dioxide 
• 174136-45-9 C₁₈H₁₃BrN₂O₃ 
• 1301603-45-1 (2E)-1-(3-methylquinoxalin-2-yl)-3-(3,4,5-trimethoxyphenyl)propenone 
• 1301603-51-9 4-(3-methylquinoxalin-2-yl)-6-(3,4,5-trimethoxyphenyl)pyrimidin-2-yl-amine 
• 1301603-58-6 4-[3-(3-methylquinoxalin-2-yl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydropyrazol-1-yl]benzenesulfonamide 
• 81810-66-4 1-(3-methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one 
• 104217-24-5 1-(3-methylquinoxalin-2-yl)ethan-1-ol 

Relevant articles and documents

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A mild and highly efficient, environmentally friendly procedure has been developed for the conversion from benzofurazan-N-oxides to quinoxaline di-N-oxides in the presence of-cyclodextrin in water at room temperature with excellent yields. The application of cyclodextrin precludes the use of organic solvent, and the catalyst can be recovered and reused in subsequent reactions with the same catalytic activity. Herein, the Beirut reaction is carried out in the medium of water for the first time. The reaction mechanism was proposed based on the inclusion complexation of-cyclodextrin with benzofurazan-N-oxides which was confirmed by 1H NMR, ultraviolet/visible spectrum, and infrared spectroscopy. Copyright

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Preparation method of mequindox

The invention provides a preparation method of mequindox. The preparation method comprises the step of performing reaction by taking ortho-nitroaniline, sodium hypochlorite and acetylacetone as raw materials, taking an NaOH/attapulgite compound as a catalyst and taking sodium carboxymethyl cellulose as a solubilizing agent and a homogenizing agent so as to obtain the mequindox. The preparation method of the mequindox, provided by the invention, realizes the purpose of one-step preparation of the mequindox, omits the intermediate treatment step of benzofurazan, and is simple in technology and high in production efficiency. The purity of the prepared mequindox product can reach 99% or more, and the total yield of the prepared mequindox product can reach 84.5% or more, which is equivalent tosingle-step yield of 90% or more, so that the prepared mequindox product has broad application prospects.

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The invention relates to a preparation method of quinohydroxylone, comprising the following steps: 1), mixing benzofuroxan and acetylacetone, adding triethylamine as a catalyst into a mixture, reacting at 40-60 DEG C, standing after reacting, filtering un