A simple method for converting nitriles to amides. Hydrolysis with potassium hydroxide in tert-butyl alcohol

Hall, John H.; Gisler, Matthias R.

doi:10.1021/jo00885a032

Cited by 108 publications

(49 citation statements)

References 1 publication

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“…[32] When these compounds are treated with dimethylformamide dimethylacetal, the bis[(dimethylamino)methylene]diamides 15 or (R)-15 are accessible in high yields, and then undergo ring closure by condensation with hydrazine. [33] The resonance of the methine proton of compound 15 is found at δ = 8.21 ppm in the 1 H NMR spectrum.…”

Section: Resultsmentioning

confidence: 99%

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A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

et al. 2009

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Chiral ligands with the 1,1′‐binaphthyl unit as the backbone play an important role in enantioselective catalysis. In this paper we present the synthesis and characterization of three novel azole‐functionalized 1,1‐binaphthyl derivatives. These systems are accessible from commercially available starting materials in not more than four steps. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

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Section: Resultsmentioning

confidence: 99%

“…The starting compounds 7·(HCl) 2 , [24] (R)-10 [27] and 14 [32] were synthesized by published procedures. All NMR spectra were recorded at room temperature.…”

Section: Methodsmentioning

confidence: 99%

A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

et al. 2009

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“…Nitriles can be hydrolyzed under either acidic or alkaline conditions to make carboxylic acids or their salts. 1,2 The final result is similar in both the cases, but the exact nature of the final product varies depending on the reaction conditions. Adiponitrile (ADN) is an important aliphatic dinitriles, which can be hydrolyzed partially or completely to produce valuable intermediates and final products.…”

Section: Introductionmentioning

confidence: 84%

Hydrolysis of Adiponitrile in Near‐critical Water

et al. 2008

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Hydrolysis of adiponitrile (ADN) in near-critical water was successfully conducted in a batch reactor. Influences of m(AND)/m(water) ratio, temperature, time, m(AND)/m(additive) ratio, kind of additive and pressure on the yield of each product were investigated. Five compounds resulting from the hydrolysis of ADN, including 5-cyanovaleramide, adipamide, adipamic acid, adipic acid and trace of 5-cyanovaleric acid, were detected by high performance liquid chromatography. The results showed that change of ADN concentration and temperature had significant influences on the yields of adipamide, adipamic acid and adipic acid; time was the significant factor for the yield of 5-cyanovaleric acid; and the yield of 5-cyanovaleramide was more dependent on the ADN concentration.

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“…Racemic naproxen nitrile (NapN) and naproxen amide (NapA) were prepared from 2-methoxynaphthalene and racemic ibuprofen nitrile from isobutylbenzene (Arsenijevic et al, 1973;Hall and Gisler, 1976;Hiyama et al, 1986). S-Naproxen was obtained from Sigma (Deisenhofen).…”

Section: Chemicalsmentioning

confidence: 99%

Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

Layh

Stolz

Böhme

et al. 1994

Journal of Biotechnology

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Bacteria were enriched from soil samples with succinate as a carbon source and racemic naproxen nitrile [2-(6-methoxy-2-naphthyl)propionitrile] as sole source of nitrogen. Since naproxen nitrile was only poorly soluble in water media amended with different water-immiscible organic phases were used for the enrichments. With pristane (2,6,10,14-tetramethylpentadecane) as the organic phase two bacterial strains were isolated (strain C3II and strain MP50) which were identified as rhodococci. Cells of both strains converted naproxen nitrile via naproxen amide to naproxen. From racemic naproxen nitrile Rhodococcus sp. C3II formed S-naproxen amide and subsequently S-naproxen. Racemic naproxen amide was hydrolysed to S-naproxen. Rhodococcus sp. MP50 converted racemic naproxen nitrile predominantly to R-naproxen amide and racemic naproxen amide to S-naproxen. With both strains racemic naproxen amide was converted to S-naproxen with an enantiomeric excess > 99% at a conversion rate up to 80% of the theoretical value. In strain C3II the enzymes which hydrolysed naproxen nitrile and naproxen amide were present only at a low constitutive level. In contrast, in Rhodococcus sp. MP50 these activities were induced when grown in the presence of various nitriles.

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A simple method for converting nitriles to amides. Hydrolysis with potassium hydroxide in tert-butyl alcohol

Cited by 108 publications

References 1 publication

A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

A Series of Novel N,N‐Donor Ligands with Binaphthyl Backbones

Hydrolysis of Adiponitrile in Near‐critical Water

Enantioselective hydrolysis of racemic naproxen nitrile and naproxen amide to S-naproxen by new bacterial isolates

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