L-Methyl-2-pyrrolidinone

Chemical Designations - Synonyms l-Methyl-2-pyrrolidinone N-Methylpyrrolidinone -Methyl-pyrrolidone -Methyl-alpha-pyrrolidone Chemioal Formula CjH,NO. 

Cyclic carbonates are prepared directly from epoxides with LiBr, CO2, NMP (l-methyl-2-pyrrolidinone), 100°. ... 

Iodoquinoxaline and 4-methyl-5-tributylstannyl-l,3-dithiol-2-one gave 2-(2-0X0-5 -methyl-1,3 -dithiol-4-yl)quinoxaline (63) (l-methyl-2-pyrrolidinone, 5°C, CuTC i, A, 40 min 44%). ... 

In a related study by the same authors, the effect of microwave irradiation on car-bodiimide-mediated esterifications on a solid support was investigated, employing benzoic acid [29]. The carboxylic acid was activated using N,N -diisopropylcarbodi-imide (DIC) through the O-acyl isourea or the symmetrical anhydride protocol (Scheme 7.9). The isourea protocol was carried out in a dichloromethane/N,N-di-methylformamide mixture in sealed vessels, whereas the anhydride reactions were carried out in l-methyl-2-pyrrolidinone (NMP) at atmospheric pressure. 

Transition metal catalysis on solid supports can also be applied to indole formation, as shown by Dai and coworkers [41]. These authors reported a palladium- or copper-catalyzed procedure for the generation of a small indole library (Scheme 7.23), representing the first example of a solid-phase synthesis of 5-arylsulfamoyl-substituted indole derivatives. The most crucial step was the cydization of the key polymer-bound sulfonamide intermediates. Whereas the best results for the copper-mediated cydization were achieved using l-methyl-2-pyrrolidinone (NMP) as solvent, the palladium-catalyzed variant required the use of tetrahydrofuran in order to achieve comparable results. Both procedures afforded the desired indoles in good yields and excellent purities [41]. 

For the preparation of the triazine membranes, the entire solid support (cellulose or polypropylene membrane) was treated with a 5 m solution of the corresponding amine in l-methyl-2-pyrrolidinone (NMP) and a 1 m solution of cesium phenolate in dimethyl sulfoxide (2 p L of each at one spot) and subsequently heated in a domestic microwave oven for 3 min. After washing the support successively with... 

Block (cap) residual lysine residues with a carboxylic acid by acylation using succinic anhydride prepared in l-methyl-2-pyrrolidinone,... 

While Diehl et al. (2001) agree that the addition of DMSO to print buffer improves spot uniformity, they argue that DMSO is also toxic and a good solvent for other materials. As a result, they explored alternative chemistries to replace DMSO and also to improve upon postprint blocking conditions in an effort to find a replacement for borate-NMP (l-methyl-2-pyrrolidinone) buffer used for preparing solutions of succinic anhydride for capping of residual amine groups. 

BASF AG CRBPII dba DBN DBU DIBAL-H DMAP DMF DMF-DMA DMPU HMDS HMPA HMPT H-LR LDA LDE LRAT MCPBA MOM NMO NMP PCC PhH = Badische Anilin- Soda Fabrik AG = cellular retinol-binding protein type II r dibenzylideneacetone = 1,5-diazabicyclo[4.3.0]non-5-ene = l,8-diazabicyclo[5.4.0]undec-7-ene = diisobutylaluminium hydride = 4-dimethylaminopyridine = A V-dimethylformamide = A,V-dimethylformamide, dimethylacetal = 1,3 -dimethyl-3,4,5,6-tetrahydro-2( 1H)-pyrimidone = hexamethyldisilazane = hexamethylphosphoramide = hexamethylphosphorous triamide = Hoffmann-La Roche = lithium diisopropylamide = lithium diethylamide = lecithin retinol acyltransferase = m-chloroperbenzoic acid = methoxymethyl = iV-methylmorpholine oxide = l-methyl-2-pyrrolidinone = pyridinium chlorochromate = benzene... 

In another study, all of the above monomers were separately polymerized as a solution in l-methyl-2-pyrrolidinone (NMP) at a concentration of 5-6% solids, and at 202 °C, overnight [14]. If the solutions were heated longer than this, they were reported to either deposit solids or else form gels. The gels from 84 and 86 were not soluble in organic solvents but did swell. On the other hand the polymer from 91 was partially soluble in NMP (approximately 50% of the polymer mass) and this soluble fraction had an inherent viscosity of 0.34 dL/g at a concentration of 0.39 g/dL. The Tg of this soluble fraction was determined to be 291 °C. No further data was provided about this latter material or any of the other monomer/polymers discussed above. 

Solubilization of the products was attempted by placing about one milligram of product in three milliliter of liquid and observing over a week. The mixtures were then heated to seventy five degrees Celsius in a water bath for two days. The liquids tested included DMSO, DMF, DMA, acetone, l-methyl-2-pyrrolidinone, diethylether, p-dioxane and water. 

Decomposition of l-methyl-2-pyrrolidinone (67) was studied by vapor-phase photolysis (72JA8281). Irradiation (Hg sensitized) led, in addition to extensive polymer formation, to the following products carbon monoxide (31%), ethene (24%), water (24%), l,3,5-trimethyl-hexahydro-l,3,5-triazine (8%), 1-methylazetidine (6%), 1-methylpyrrole, and methane (<1%). The mechanism of formation of most of these products involves... 

A method has been reported for the solid-phase synthesis of tetrazolo[5,1 -tf]phthalazine derivatives 501 based on the cyclization of resin-bound chlorophthalazines 500 with NaN3 in l-methyl-2-pyrrolidinone (NMP) at 120°C (Scheme 63) <2005TL3107>. 

Chloromethyl salicylate Potassium carbonate l-Methyl-2-pyrrolidinone N-Methyltropamine... 

The 5-chloro-2-(2-methyl-2-propenyloxy)benzoic acid, methyl ester was heated at reflux for 6 h in l-methyl-2-pyrrolidinone. The mixture was then vacuum distilled and the fraction collected and the desired 2-hydroxy-5-chloro-3-(2-methyl-2-propenyl)benzoic acid, methyl ester was obtained. 

The Shibasaki cychzation of mc.vo-cyclohexa-1,4-dienes in the presence of a chiral palladium complex and silver carbonate in l-methyl-2-pyrrolidinone is probably the first example of an enantioselective Heck reaction (Scheme 10.34).60 The enantiomeric excess could be slightly improved by replacing the chiral phosphine ligand BINAP with the corresponding less coordinating arsine ligand, as well as replacing silver carbonate with silver phosphate.61,62... 

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