457-74-9

Upstream product

• 105-37-3 Ethyl propionate 
• 371-40-4 4-fluoroaniline 
• 123-62-6 propionic acid anhydride 
• 328393-70-0 1-(4-fluorophenyl)propan-1-one oxime 
• 802294-64-0 propionic acid 
• 350-46-9 4-Fluoronitrobenzene 
• 107-12-0 propiononitrile 
• 1195-45-5 para-fluorophenyl isocyanate 
• 999-75-7 ethylzinc iodide 

Downstream Products

• 1383479-31-9 C₂₈H₃₀N₂O₄ 
• 1693-37-4 parapropamol 

Relevant academic research and scientific papers

Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates

Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.

An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine

A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.

An iron-catalysed synthesis of amides from nitriles and amines

The cheap, commercially available iron complex, Fe(NO3)3·9H2O, has been used to catalyse the formation of amides by the addition of amines to nitriles.

Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile

(Chemical Equation Presented) An acetonitrile solution of mercury(II) chloride has been found to catalyze efficiently the conversion of a diverse range of ketoximes into their corresponding amides/lactams.

A novel synthesis of N-arylamides from nitroarenes via reductive N-acylation with red phosphorus and iodine

A series of N-arylamides and imides were synthesized via reductive N-acylation of nitroarenes with red phosphorus and carboxylic acids, catalyzed by iodine or iodides; an I /I° redox cycle was proposed to promote the reaction. Georg Thieme Verlag Stuttgart.

Chemoselective acylation of amines in aqueous media

Amines are efficiently acylated by both cyclic and acyclic anhydrides by dissolving them in an aqueous medium with the help of a surfactant, sodium dodecyl sulfate (SDS). Cyclic and acyclic anhydrides react with equal ease with an amine, and amines with various stereo-electronic factors react at the same rates with an anhydride. Chemoselective acylation of amines in the presence of phenols and thiols and of thiols in the presence of phenols has been achieved. No acidic or basic reagents are used during the reaction. No Chromatographic separation is required for isolation of the acylated products. Reactions in a neutral aqueous medium, easy isolation of products, and innocuous by-products make the present method a green chemical process. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Rhodium-catalyzed Beckmann rearrangement

equation presented Beckmann rearrangement of oxime is catalyzed by [RhCl(cod)]2, trifluoromethanesulfonic acid, and tris(p-tolyl)phosphine in refluxing dichloroethane, giving the corresponding amide in good yield. Product/acid ratios of 10:20 can be attained in the reaction of benzophenone oximes.

Efficient synthesis of aromatic sec-amides from esters: Synthetic utility of bislithium amides

Convenient, efficient preparation of aromatic sec-amides from esters has been accomplished using dilithium amides which are easily prepared by treatment of aromatic amines with 2 equiv of BuLi in THF. This new method allows a facile formation of amide bond even with sterically hindered esters.