5437-38-7

Basic information

• Product Name: 3-Methyl-2-nitrobenzoic acid
• Synonyms: 3-METHYL-2-NITROBENZOIC ACID;2-NITRO-3-METHYLBENZOIC ACID;2-NITRO-M-TOLUIC ACID;3-Methyl-2-NitrobenzoicAcid98%;3-Methyl-2-Nitrobenzoic Acid 98%;3-Methyl-2-nitrobenzoic;3-METHY-2-NITROBENZOICACID;3-Methyl-2-nitrobenz
• CAS NO: 5437-38-7
• Molecular Formula: C₈H₇NO₄
• Molecular Weight: 181.15
• EINECS: 226-610-9
• Product Categories: FINE Chemical & INTERMEDIATES;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;Benzoic acid;Organic acids;Building Blocks;C8;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 5437-38-7.mol

Chemical Properties

• Melting Point: 220-223 °C(lit.)
• Boiling Point: 314.24°C (rough estimate)
• Flash Point: 153.358 °C
• Appearance: white to slightly yellow crystalline powder
• Density: 1.4283 (rough estimate)
• Vapor Pressure: 3.44E-05mmHg at 25°C
• Refractive Index: 1.5468 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 2.26±0.10(Predicted)
• Water Solubility: <0.1 g/100 mL at 22℃
• BRN: 1960698
• CAS DataBase Reference: 3-Methyl-2-nitrobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-2-nitrobenzoic acid(5437-38-7)
• EPA Substance Registry System: 3-Methyl-2-nitrobenzoic acid(5437-38-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39-22-37
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 5437-38-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Methyl-2-nitrobenzoic acid is used as a building block for the synthesis of novel Indolin-2-one derivatives, which act as protein tyrosine phosphatase 1B inhibitors. These inhibitors play a crucial role in the development of potential therapeutic agents for various diseases, including diabetes and obesity, by modulating the activity of specific enzymes involved in these conditions.
Used in Chemical Synthesis:
3-Methyl-2-nitrobenzoic acid is also utilized in the chemical synthesis of various compounds, contributing to the development of new materials and products across different industries. Its versatile chemical properties make it a valuable component in the creation of a wide range of chemical entities.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

3-Methyl-2-nitrobenzoic acid is a nitrated carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.

Fire Hazard

Information concerning the flash point of 3-Methyl-2-nitrobenzoic acid is not available. 3-Methyl-2-nitrobenzoic acid is probably combustible.

Purification Methods

Recrystallise it from EtOH. The methyl ester has m 74o (from MeOH), and the amide [60310-07-8] M 180.1, has m 192o (needles from H2O, prisms from EtOH). [Beilstein 9 H 480, 9 IV 1722.]

InChI:InChI=1/C8H7NO4/c1-5-3-2-4-6(8(10)11)7(5)9(12)13/h2-4H,1H3,(H,10,11)/p-1

Synthetic route

methyl 3-methyl-2-nitrobenzoate (5471-82-9) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With sodium hydroxide In methanol at 20℃; Reagent/catalyst;	80.96%

m-Toluic acid (99-04-7) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With nitric acid at -10℃; for 1h; Temperature;	79%
With nitric acid at -10℃; for 1h; Inert atmosphere;	50%
With nitric acid at -10℃; for 1h;	49%

n-butyl 3-methyl-2-nitrobenzoate → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With hydrogenchloride In ethanol; water at 20℃;	78.62%

m-Toluic acid (99-04-7) → 5-methyl-2-nitrobenzoic acid (3113-72-2) + 3-methyl-4-nitrobenzoic acid (3113-71-1) + 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With guanidine nitrate Reagent/catalyst;	A 54% B 13% C 33%
With sulfuric acid; uronium nitrate at 25℃; for 24h;
With guanidine nitrate In sulfuric acid at 0 - 20℃;
With dinitrogen pentoxide In tetrachloromethane at 50℃; for 2h; regioselective reaction;

m-Toluic acid (99-04-7) → 5-methyl-2-nitrobenzoic acid (3113-72-2) + 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With uronium nitrate	A 45% B 45%
With nitric acid
With sulfuric acid; potassium nitrate

1-methyl-4-nitrosobenzene (623-11-0) + 4-methyl-3-nitro-tropolone (833454-20-9) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

2,6-dimethylnitrobenzene (81-20-9) → 3-methyl-2-nitrobenzoic acid (5437-38-7) + 2,4-dinitro-m-xylene (603-02-1)

Conditions	Yield
With nitric acid

m-Toluic acid (99-04-7) → 3-methyl-4-nitrobenzoic acid (3113-71-1) + 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With nitric acid

para-dinitrobenzene (100-25-4) + 3-Methyl-2-nitro-benzoic acid (58833-57-1) → 3-methyl-2-nitrobenzoic acid (5437-38-7) + 1,4-dinitroanthracene radical anion (100-25-4)

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

(4-nitrophenyl)ethanone (100-19-6) + 3-Methyl-2-nitro-benzoic acid (58833-57-1) → 3-methyl-2-nitrobenzoic acid (5437-38-7) + p-nitroacetophenone anion radical (100-19-6)

Conditions	Yield
In water; isopropyl alcohol Rate constant; Thermodynamic data; Irradiation; electron transfer reaction ΔE exc.;

3-methyl-2-nitrobenzoyl chloride (50424-93-6) + 3-methylantranilic acid (4389-45-1) → 3-methyl-2-nitrobenzoic acid (5437-38-7) + 3-methyl-N-(3-methyl-2-nitrobenzoyl)anthranilic acid (78876-98-9)

Conditions	Yield
With potassium hydroxide In water; benzene for 1.33333h; Title compound not separated from byproducts;

nitric acid (7697-37-2) + m-Toluic acid (99-04-7) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

sulfuric acid (7664-93-9) + m-Toluic acid (99-04-7) + potassium nitrate → 5-methyl-2-nitrobenzoic acid (3113-72-2) + 3-methyl-2-nitrobenzoic acid (5437-38-7)

vic nitro-m-xylene → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
With nitric acid

3-methyl-2-nitro-benzaldehyde (5858-27-5) + KMnO4-solution → 3-methyl-2-nitrobenzoic acid (5437-38-7)

3-Methylbenzonitrile (620-22-4) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: concentrated hydrochloric acid / im Druckrohr 2: fuming nitric acid View Scheme

m-Toluic acid (99-04-7) → 5-methyl-2-nitrobenzoic acid (3113-72-2) + 3-methyl-4-nitrobenzoic acid (3113-71-1) + 3-methyl-2-nitrobenzoic acid (5437-38-7) + 3-methyl-2,6-dinitrobenzoic acid (3478-09-9)

Conditions	Yield
With uronium nitrate In sulfuric acid at 0 - 20℃;

2,6-dimethylnitrobenzene (81-20-9) → 3-methyl-2-nitrobenzoic acid (5437-38-7) + 2-nitroisophthalic acid (21161-11-5)

Conditions	Yield
With cobalt(II) acetate; acetaldehyde; acetic acid In water at 100℃; for 4h; Temperature; Reagent/catalyst; Sealed tube; Inert atmosphere;

1-methoxycarbonyl-3-methylbenzene (99-36-5) → 3-methyl-2-nitrobenzoic acid (5437-38-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: nitric acid; acetic anhydride / dichloromethane / 0.25 h / 40 - 50 °C 2: sodium hydroxide / methanol / 20 °C View Scheme

3-methyl-2-nitrobenzoic acid (5437-38-7) → 3-methyl-2-nitrobenzoyl chloride (50424-93-6)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In 1,2-dichloro-ethane for 3h; Reflux;	100%
With thionyl chloride In 1,2-dichloro-ethane; N,N-dimethyl-formamide for 3h; Reflux;	95.2%
With phosphorus pentachloride

3-methyl-2-nitrobenzoic acid (5437-38-7) → 2-methyl-6-hydroxymethyl-1-nitrobenzene (80866-76-8)

Conditions	Yield
With borane-THF In tetrahydrofuran Inert atmosphere; Reflux;	100%
With dimethylsulfide borane complex In tetrahydrofuran at 80℃; for 3h; Inert atmosphere;	90%
Multi-step reaction with 2 steps 1: SOCl2, DMF 2: 61 percent / NaBH4 / dimethylformamide; tetrahydrofuran / 3 h / Ambient temperature View Scheme
With borane-THF In tetrahydrofuran at 0℃; Inert atmosphere; Reflux;

methanol (67-56-1) + 3-methyl-2-nitrobenzoic acid (5437-38-7) → methyl 3-methyl-2-nitrobenzoate (5471-82-9)

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 10h; Reagent/catalyst; Time; Inert atmosphere;	99%
With acetyl chloride at 0℃; for 20h; Reflux;	95%
With sulfuric acid for 24h; Heating;	89%

3-methyl-2-nitrobenzoic acid (5437-38-7) → 3-methylantranilic acid (4389-45-1)

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 760 Torr;	99%
With hydrogen; palladium on activated charcoal In ethanol at 20℃; under 25857.4 Torr;	99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 760.051 Torr;	99%

3-methyl-2-nitrobenzoic acid (5437-38-7) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N,3-dimethyl-2-nitrobenzamide (1355966-30-1)

Conditions	Yield
Stage #1: 3-methyl-2-nitrobenzoic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 0.5h;	98%

3-methyl-2-nitrobenzoic acid (5437-38-7) → potassium 2-nitro-3-methylbenzoate (80841-44-7)

Conditions	Yield
With potassium tert-butylate In ethanol at 20℃; for 3h;	97%
With potassium tert-butylate In ethanol at 20℃; for 3h;	93%
With potassium tert-butylate In ethanol at 20℃; for 3h; Inert atmosphere;	91%

3-methyl-2-nitrobenzoic acid (5437-38-7) + α-bromoacetophenone (70-11-1) → phenacyl 3-methyl-2-nitrobenzoate

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	95.2%

3-methyl-2-nitrobenzoic acid (5437-38-7) → 3-Methyl-2-nitrobenzenecarboxamide (60310-07-8)

Conditions	Yield
With ammonia; triethylamine In tetrahydrofuran; chloroformic acid ethyl ester	95%
Stage #1: 3-methyl-2-nitrobenzoic acid With isopropyl chloroformate; triethylamine In dichloromethane at 0℃; for 1h; Stage #2: With ammonium hydroxide In dichloromethane at 0℃; for 0.5h;	84%
Stage #1: 3-methyl-2-nitrobenzoic acid With oxalyl dichloride In dichloromethane at 20 - 25℃; for 1h; Stage #2: With ammonium hydroxide In dichloromethane at 20℃; for 0.5h;	60.6%

3-methyl-2-nitrobenzoic acid (5437-38-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → N,N-dimethyl-2-nitro-3-methylbenzamide

Conditions	Yield
With tert.-butylhydroperoxide; iron(III) chloride In pyridine; water; toluene at 85℃; for 8h; Inert atmosphere; Sealed tube;	93%
With trichlorophosphate at 120℃; for 1h; Sealed tube;	90%
With trichlorophosphate at 120℃; for 1h;	90%

3-methyl-2-nitrobenzoic acid (5437-38-7) + para-bromophenacyl bromide (99-73-0) → p-bromophenacyl 3-methyl-2-nitrobenzoate

Conditions	Yield
With potassium fluoride In N,N-dimethyl-formamide for 0.5h; Ambient temperature;	91%

3-methyl-2-nitrobenzoic acid (5437-38-7) + methylamine (74-89-5) → N,3-dimethyl-2-nitrobenzamide (600126-70-3)

Conditions	Yield
Stage #1: 3-methyl-2-nitrobenzoic acid With thionyl chloride In toluene at 90 - 100℃; Stage #2: methylamine In dichloromethane; water at 0 - 10℃;	90%
Stage #1: 3-methyl-2-nitrobenzoic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 10℃; Stage #2: methylamine In tetrahydrofuran

3-methyl-2-nitrobenzoic acid (5437-38-7) + dimethyl sulfate (77-78-1) → methyl 3-methyl-2-nitrobenzoate (5471-82-9)

Conditions	Yield
Stage #1: 3-methyl-2-nitrobenzoic acid With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In acetone for 4h; Reflux;	90%

3-methyl-2-nitrobenzoic acid (5437-38-7) + allyl alcohol (107-18-6) → allyl 3-methyl-2-nitrobenzoate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification;	85%

3-methyl-2-nitrobenzoic acid (5437-38-7) + tert-butyl alcohol (75-65-0) → tert-butyl N-(3-methyl-2-nitrophenyl)carbamate

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In tert-butyl alcohol at 90℃; for 18h; Temperature; Inert atmosphere;	84%
With diphenyl phosphoryl azide; triethylamine at 82℃; for 10h;	82%

3-methyl-2-nitrobenzoic acid (5437-38-7) + (2E)-3-phenyl-2-propen-1-ol (4407-36-7) → cinnamyl 3-methyl-2-nitrobenzoate (1620682-47-4)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Steglich Esterification;	83%

Upstream product

• 623-11-0 1-methyl-4-nitrosobenzene 
• 833454-20-9 4-methyl-3-nitro-tropolone 
• 81-20-9 2,6-dimethylnitrobenzene 
• 99-04-7 m-Toluic acid 
• 100-25-4 para-dinitrobenzene 
• 58833-57-1 3-Methyl-2-nitro-benzoic acid 
• 100-19-6 (4-nitrophenyl)ethanone 
• 50424-93-6 3-methyl-2-nitrobenzoyl chloride 
• 4389-45-1 3-methylantranilic acid 
• 7697-37-2 nitric acid 
• 7664-93-9 sulfuric acid 
• 5858-27-5 3-methyl-2-nitro-benzaldehyde 
• 620-22-4 3-Methylbenzonitrile 
• 99-36-5 1-methoxycarbonyl-3-methylbenzene 

Downstream Products

• 5471-82-9 methyl 3-methyl-2-nitrobenzoate 
• 21161-11-5 2-nitroisophthalic acid 
• 60310-07-8 3-Methyl-2-nitrobenzenecarboxamide 
• 50424-93-6 3-methyl-2-nitrobenzoyl chloride 
• 4389-45-1 3-methylantranilic acid 
• 92891-23-1 2-nitro-3-trifluoromethyl-toluene 
• 95-53-4 o-toluidine 
• 908597-10-4 2,5-dibromo-3-methyl benzoic acid methyl ester 
• 908597-09-1 2,5-dibromo-3-methylbenzoic acid 
• 95541-19-8 2-acetylamino-3-methyl-5-nitrobenzoic acid 
• 67081-69-0 2-acetylamino-3-methylbenzoic acid 
• 70343-14-5 2-amino-3-methyl-5-nitrobenzoic acid 
• 90414-59-8 2-Iodo-3-methyl-5-nitrobenzoic acid 
• 206548-13-2 2-amino-5-bromo-3-methylbenzoic acid 

Relevant articles and documents

Preparation method of 2-amino-3-methyl-5-chlorobenzoic acid

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention comprises the steps of mixing m-toluic acid and nitric acid, and carrying out nitration reaction to obtain 2-nitro-3-methyl benzoic acid, wherein the mass concentration of the nitric acid is 60-75%; mixing the 2-nitro-3-methyl benzoic acid, a hydrogenation reduction reaction solvent and a hydrogenation catalyst, and carrying out hydrogenation reduction reaction in a hydrogen atmosphere to obtain 2-amino-3-methyl benzoic acid; and mixing the 2-amino-3-methyl benzoic acid, a chlorination reagent, benzoyl peroxide and a chlorination reaction solvent, and carrying out a chlorination reaction to obtain the 2-amino-3-methyl-5-chlorobenzoic acid. The preparation method provided by the invention has the advantages of cheap and easily available reaction raw materials, high product yield and high purity, and is easy for industrial production.

PROCESS FOR THE PREPARATION OF CHLORANTRANILIPROLE

The present invention relates to two novel, efficient and one-pot methods for synthesizing chlorantraniliprole. In the first scheme, Chlorantraniliprole is prepared by a novel telescopic process starting from 3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxylic acid a key raw material-A (Key RM-A). In the second scheme, starting from Key RM-A, the process steps use of a novel variant of anthranilic acid (Methyl 2-amino-5-chloro-3-methylbenzoate), to get Chlorantraniliprole. Furthermore, the present invention also relates to the synthesis of key starting material for the synthesizing chlorantraniliprole in-situ. All the in-situ steps of the disclosed synthesis methods obtain good yield, without using any expensive reagent or base or harsh reaction conditions, which makes the process simple, environment friendly and more cost effective. With this process the production cost of chlorantraniliprole and its intermediates is substantially reduced; fewer by-products are formed during its synthesis and since it's a one-pot reaction, isolation and purification are easy to achieve.

Method for synthesizing 2-nitro-3-methylbenzoic acid

The invention discloses a method for synthesizing 2-nitro-3-methylbenzoic acid. The method comprises that powdery meta-methylbenzoic acid and nitric acid undergo a reaction at -30 to -15 DEG C to produce a nitrification reaction solution, and the nitrification reaction solution is separated and purified to form a 2-nitro-3-methylbenzoic acid product. The method has simple processes, is easy to operate, has a high conversion rate of m-methylbenzoic acid, has high selectivity of 2-nitro-3-methylbenzoic acid, and has obvious environmental protection effects and significant economic benefits.

Preparation method of highly selective 3-methyl-2-nitrobenzoic acid

The invention discloses a preparation method of 3-methyl-2-nitrobenzoic acid. 3-methylbenzoic acid alkyl ester is used as raw material in nitrification, two-grade selectivity and high yield are realized, and the amount of waste acid was reduced. In nitrification product, only 3-methyl 2-nitrobenzoic acid alkyl ester and 3-methyl-4-nitrobenzoic acid alkyl ester are hydrolyzed after separation to obtain 3-methyl 2-Nitrobenzoic acid and 3-methyl-4-nitrobenzoic acid. The process is simple, and suitable for industrial production.

PROCESS TO PREPARE 3-METHYL-2-NITROBENZOIC ACID BY AIR OXIDATION

A method for preparing 3-methyl-2-nitrobenzoic acid is disclosed wherein 1, 3 -dimethyl-2-nitrobenzene is combined with an oxidation catalayst in the presence of an oxygen source and an initiator, provided that less than 99% of the 1,3 -dimethyl-2- nitrobenzene is oxidized. A method for preparing compounds of Formula 7 and Formula 11 is also disclosed wherein the method is characterized by using 3-methyl-2-nitrobenzoic acid as prepared by the method disclosed above. wherein R1 is C1-C7 alkyl, C3-C6 cycloalkyl or C4-C7 alkylcycloalkyl

An "ortho effect" in electrophilic aromatic nitrations: Theoretical analysis and experimental validation

Usually, a π-donor substituent acts as an ortho/para directing group in an electrophilic aromatic substitution reaction, and a π-acceptor substituent acts as a meta directing group. Interestingly, when a π-acceptor substituent is meta to a π-donor substituent, certain electrophilic aromatic nitration occurs ortho to the π-acceptor substituent rather than para . The "ortho effect", highlighted in various textbooks, has been tentatively analyzed here based on ab initio calculations. The reliability of the calculations was verified by the corresponding experimental data, including a newly-designed electrophilic aromatic nitration that also gave reasonable product distributions.

A significant improvement in enantioselectivity, yield, and reactivity for the copper-bi-o-tolyl bisoxazoline-catalyzed asymmetric allylic oxidation of cyclic olefins using recoverable SBA-15 mesoporous silica material

A series of chiral bi-o-tolyl bisoxazoline ligands 1 and 2 were conveniently synthesized on a gram scale from inexpensive and commercially available 3-methyl benzoic acid in eight steps. The catalytic and induced asymmetric effects of the chiral copper (I) complexes of these ligands on the asymmetric allylic oxidation of cycloolefins were investigated in the presence of various nano-sized additives. When SBA-15 mesoporous silica was used in conjunction with these ligands very highly enantioselectivities (up to 97% ee) and excellent yields (up to 99%) of the corresponding chiral allylic esters were obtained in a reasonably short period of time.

Regioselectivity nitration of aromatics with N2O5 in PEG-based dicationic ionic liquid

Regioselective mononitration of simple aromatic compounds has been investigated with N2O5 as nitrating agent and a new PEG200-based dicationic acidic ionic liquid (PEG200-DAIL) as catalyst. The results of experiments show that this nitration system can significantly improve the para-selectivity of alkyl-benzenes and the ortho-selectivity of halogenated-benzenes. The PEG200-DAIL exhibits recyclable temperature-dependant phase behavior in CCl4 solvent, and it can be recycled without apparent loss of catalytic activity, and only 5% loss of weight is observed after six times recycling.

INHIBITORS OF STEAROYL-COA DESATURASE

Provided herein are compounds of the formula (I): as well as pharmaceutically acceptable salts thereof, wherein the substituents are as those disclosed in the specification. These compounds, and the pharmaceutical compositions containing them, are useful for the treatment of diseases such as, for example, obesity.

Aromatic nitration using nitroguanidine and EGDN

Acid catalyzed nitration has been examined using a variety of novel nitration agents: guanidine nitrate (GN) and nitroguanidine (NQ) as well as the simple nitrate ester, ethylene glycol dinitrate (EGDN). Reactions with either activated or deactivated aromatic substrates proceed rapidly and in high yield. Regioselectivity was similar for all nitrating agents examined. The synthetic advantages of liquid EGDN include high solubility in organic solvents, strong nitration activity and ease of preparation.