An efficient Pd-catalyzed hydration of nitrile with acetaldoxime

A mild hydration of nitriles catalysed by copper(ii) acetate

“…This evidence indicates that in the hydration pathway water is not acting as nucleophile. These results will support the nucleophilic attack of the NEt 2 OH followed by a radical 11,12 or rearrangement pathway facilitated by the Lewis acid. 2,14 Further studies to uncover the more plausible pathway are still undergoing.…”

“…1b, 2,11,12 Based on these results and our earlier work using hydroxylamine hydrochloride to catalyse transamidation, 2 as well as the conversion of nitriles into secondary amides using hydroxylamine, 13 we decided to explore this reactivity for the synthesis of primary amides. In a first approach, p-methoxybenzonitrile (1) was treated with 16 equivalents of hydroxylamine.…”

A mild alkaline hydrolysis of N- and N,N-substituted amides and nitriles

“…The hydrolysis of amides and nitriles is a well studied reaction and numerous methods have been developed. [4][5][6][7][8][9][10][11][12][13][14] Among them, the use of sodium peroxide 4 and of phthalic anhydride 5 for the amide hydrolysis have been described, while nitriles can also be converted to amides by catalyzed hydration, [6][7][8][9] enzymatically 10 and on unactivated alumina. 11 Ames and Islip in their temperature, while primary and secondary amides were extremely resistant under the same conditions.…”

Palladium‐Catalyzed Aminocarbonylation of Benzyl Chlorides using Ammonia

“…3-Methoxybenzyl chloride gave 3-methoxyphenylacetamide in 98 % yield (Table 3, entry 5). Benzyl chlorides with electronwithdrawing groups also successfully gave the corresponding products in 83-94 % yields (Table 3, entries [6][7][8]. Not surprisingly, aminocarbonylation of the chloride-substituted substrate proceeded chemoselectively (Table 3, entry 8).…”

“…[5h, i] Primary benzyl amides represent interesting pharmaceutical compounds. [6] Traditionally, these compounds are synthesized by hydration of the corresponding benzyl cyanides [7] or condensation of 2-arylacetic acids with ammonia. [8] In addition, carbonylation of inexpensive benzyl chlorides with ammonia offers a straightforward access to this class of compounds.…”