42469-26-1

Basic information

• Product Name: N-(2-hydroxyethyl)-4-methylbenzamide
• Synonyms: N-(2-hydroxyethyl)-4-methylbenzamide;IDI1_016251;Maybridge3_004864;ZINC03138367
• CAS NO: 42469-26-1
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.21572
• Mol File: 42469-26-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(2-hydroxyethyl)-4-methylbenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-hydroxyethyl)-4-methylbenzamide(42469-26-1)
• EPA Substance Registry System: N-(2-hydroxyethyl)-4-methylbenzamide(42469-26-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 42469-26-1(Hazardous Substances Data)

Upstream product

• 141-43-5 ethanolamine 
• 99-94-5 p-Toluic acid 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 874-60-2 4-methyl-benzoyl chloride 
• 619-55-6 para-methylbenzamide 
• 1644630-66-9 C₁₄H₁₀ClNO₄ 

Downstream Products

• 10200-70-1 2-(4-methylphenyl)-4,5-dihydro-1,3-oxazole 
• 161194-79-2 N-(2-chloroethyl)-4-methylbenzamide 
• 27115-50-0 N-(4-methylbenzoyl)glycine 

Relevant articles and documents

Design, synthesis and biological activity evaluation of a new class of 2,4-thiazolidinedione compounds as insulin enhancers

Diabetes mellitus (DM) is a global disease with a high incidence of type 2 diabetes. Current studies have shown that insulin enhancers play an important role in the treatment of type 2 diabetes and have great importance in the improvement of type 2 diabetes. In this research, Rosiglitazone was taken as the lead compound, and the structure was modified by using the bioisostere principle, and a new class of 2,4-thiazolanedione compound was designed and synthesised. The novel series of compounds were studied for their biological activities in vitro and in vivo. In vitro tests, the biological activities showed that the target compounds have good selective activation of peroxisome-proliferator-activated receptor γ (PPARγ), such as the compounds 6a, 6e, 6f, 6g and 6i, especially the compound 6e to PPARγ was EC50 = 0.03 ± 0.01 μmol/L in vitro. Then, in vivo biological activities’ test results showed that the tendency of increasing in blood sugar had an obvious inhibiting effect, and had a significant insulin hypoglycaemic effect of enhancing and extending the exogenous. In addition, the results of cytotoxicity tests and acute toxicity tests (LD50) showed that these compounds belong to the low toxicity compounds.

Metal-Free O-Selective Direct Acylation of Amino Alcohols Through Pseudo-Intramolecular Process

Efficient α-aryl-β-keto ester acylation of amine accompanied by the elimination of ethyl phenylacetate was achieved owing to the pseudo-intramolecular process. The eliminated ethyl phenylacetate could be recycled by conversion into an α-aryl-β-keto ester upon treatment with an acyl chloride in the presence of lithium bis(trimethylsilyl)amide, by which the atom economy considerably increased. Acylation using an α-aryl-β-keto ester is highly sensitive to the bulkiness of the nucleophile, which facilitated the regioselective-acylation of the less hindered amino group in diamine without protecting the other. The transacylation of α-aryl-β-keto ester with N-alkylamino alcohol resulted in chemoselective O-acylation without protecting the amino group because the hydroxy group was attracted to the reaction site of the keto ester by forming an ammonium salt. Transacylation was demonstrated to be a practically useful tool for organic synthesis because this protocol can be conducted under mild conditions with simple manipulations in the absence of any additives such as metal catalyst and base.

Microwave-Assisted Synthesis of 2-Aryl-2-oxazolines, 5,6-Dihydro-4H-1,3-oxazines, and 4,5,6,7-Tetrahydro-1,3-oxazepines

The first general procedure for the synthesis of 5- to 7-membered cyclic iminoethers by microwave-assisted cyclization of ω-amido alcohols promoted by polyphosphoric acid (PPA) esters is presented. 2-Aryl-2-oxazolines and 5,6-dihydro-4H-1,3-oxazines were efficiently prepared using ethyl polyphosphate/CHCl3. Trimethylsilyl polyphosphate in solvent-free conditions allowed for the synthesis of hitherto-unreported 4,5,6,7-tetrahydro-1,3-oxazepines. The method involves good to excellent yields and short reaction times.The reaction mechanism and the role of PPA esters were investigated in a chiral substrate.

A Mild and Regioselective Route to Functionalized Quinazolines

A Rh-catalyzed ortho-amidation cyclocondensation sequence gave a range of 4-aminoquinazolines in high yield. The method features a remarkably mild C(sp2)-H activation step and can be exploited to rapidly access compounds with established biological activity.

Hydrogen bond organocatalysis of benzotriazole in transamidation of carboxamides with amines

A new method of transamidation of carboxamides with amines catalyzed by benzotriazole has been developed.

The α-effect in hydrazinolysis of 4-chloro-2-nitrophenyl x-substituted-benzoates: Effect of substituent x on reaction mechanism and the α-effect

Second-order rate constants (kN) have been measured spectrophotometrically for the reaction of 4-chloro-2- nitrophenyl X-substituted-benzoates (6a-6h) with a series of primary amines including hydrazine in 80 mol % H2O/20 mol % DMSO at 25.0°C. The Bronsted-type plot for the reaction of 4-chloro-2-nitrophenyl benzoate (6d) is linear with βnuc = 0.74 when hydrazine is excluded from the correlation. Such a linear Bronsted-type plot is typical for reactions reported previously to proceed through a stepwise mechanism in which expulsion of the leaving group occurs in the rate-determining step (RDS). The Hammett plots for the reactions of 6a-6h with hydrazine and glycylglycine are nonlinear. In contrast, the Yukawa-Tsuno plots exhibit excellent linear correlations with ?X = 1.29-1.45 and r = 0.53-0.56, indicating that the nonlinear Hammett plots are not due to a change in RDS but are caused by resonance stabilization of the substrates possessing an electron-donating group (EDG). Hydrazine is ca. 47-93 times more reactive than similarly basic glycylglycine toward 6a-6h (e.g., the α-effect). The α-effect increases as the substituent X in the benzoyl moiety becomes a stronger electronwithdrawing group (EWG), indicating that destabilization of the ground state (GS) of hydrazine through the repulsion between the nonbonding electron pairs on the two N atoms is not solely responsible for the substituent-dependent α-effect. Stabilization of transition state (TS) through five-membered cyclic TSs, which would increase the electrophilicity of the reaction center or the nucleofugality of the leaving group, contributes to the α-effect observed in this study.

NOVEL METHODS FOR THE TREATMENT OF INFLAMMATORY DISEASES

Methods of inhibiting the cytokine or biological activity of Macrophage Migration Inhibitory Factor (MIF) comprising contacting MIF with a compound of formula (I) are provided. The invention also relates to methods of treating diseases or conditions where MIF cytokine or biological activity is implicated comprising administration of compounds of formula (I), either alone or as a part of combination therapy. Novel compounds of formula (I) are also provided for.

1H NMR spectroscopic investigation of the mechanism of 2-substituted-2- oxazoline ring formation and of the hydrolysis of the corresponding oxazolinium salts

Chlorination of 2-hydroxyethylamides containing electrondonor substituents such as alkyl, phenyl or alkyl- or alkyloxy-substituted phenyl at 23 °C with SOCl2 proceeds via 2-substituted-2-oxazolinium hydrochlorides that can be transformed in sit

A novel electrochemical method for benzoylation of aminoalcohols with methyl benzoates at room temperature

A novel electrochemical method of benzoylating aminoalcohols 2 by use of methyl benzoates 1 at room temperature was developed. 2-Aminoethanols 2 (n=0, R3=H) and 3-aminopropanols 2 (n=1, R3=H) gave the corresponding benzamides 4, as a result of electrochemical transesterification followed by O,N-acyl migration.In contrast, o- and m-aminobenzylalcohols (7a and 7b) and trans-4-(aminomethyl)cyclohexanemethanol (8a) afforded the corresponding benzoic esters, since their acyl migration is hindered.A local anesthetic, procaine, was prepared by using this electrochemical reaction.A mechanism for electrochemical transesterification, which involves a formation of alcoholate anion by a one-electron reduction of alcohol, is presented.

ELECTROCHEMICAL AMIDATION OF ESTERS

Amidation reactions between ester and amine, both aliphatic and aromatic, which do not happen non-electrochemically at room temperature, took place merely by passing electric current in cathodic compartment.