Solid-phase catalysis of the hydrolysis of nitriles to amides

Cook, M. J.; Forbes, E.J.; Khan, Gul Majid

doi:10.1039/c19660000121

Cited by 14 publications

(13 citation statements)

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“…A new and potentially useful synthesis for amides became available a few years ago when we obtained a patent (Haefele, 1968) on the manganese dioxide catalyzed hydration of nitriles. Shortly after our application was filed, another group (Cook et al, 1966) published the results of essentially* identical findings in their laboratory.…”

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confidence: 82%

Catalyzed Hydration of Nitriles to Amides

Haefele¹,

Young²

1972

Product R&D

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A simple, convenient, and inexpensive general process for the hydration of nitriles to amides under the influence of a manganese dioxide catalyst is described. The reaction can be conducted in a simple fixed-bed continuous reactor at moderate temperatures with reaction times of a few hours. An aqueous solution or suspension of the nitrile is employed. In most instances essentially quantitative yields of amide are obtained with complete freedom from coproducts or side reactions. The catalyst is commercially available and has a long useful life.

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confidence: 82%

Catalyzed Hydration of Nitriles to Amides

Haefele¹,

Young²

1972

Product R&D

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“…Methyl 3-(p -Nitrophenyl)-3-[(p -nitrobenzoyl)oxy ]-2cyanopropenoate (3). A solution of 75 g (0.4 mol) of p-nitrobenzoyl chloride (Aldrich Chemical Co.) and methyl cyanoacetate (20 g, 0.2 mol) (Aldrich Chemical Co.) in dry benzene (300 mL) was cooled to 10 °C.…”

Section: Methodsmentioning

confidence: 99%

“…Sodium (11.6 mg, 0.5 mmol) was added, and after its dissolution, 3 (200 mg, 0.5 mmol) in dry THF (2 mL) was added. After the mixture was warmed to 35-40 °C for a few min, the characteristic yellow color of 1 began to develop.…”

Section: Methodsmentioning

confidence: 99%

Acyl-oxygen cleavage in the alkaline hydrolysis of activated vinyl esters

Strauss¹,

Rappoport²

1982

J. Org. Chem.

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carried out are summarized in Table I.It should be noted that under these reaction conditions allylic C-H insertion, to produce 9, competes effectively with the usually efficient7® intramolecular cyclopropanation.8 Methylene C-H insertion is substantially more rapid than methyl C-H insertion,9 allowing clean formation of 10. While it might be extrapolated that methine should be more efficient than methylene insertion, ring-size effects predominate, so that 7 is formed from 2.The functionalized cyclopentanes produced by this cyclization should be versatile intermediates for elaboration to complex natural products. Keto ester 10, for example, prepared by Tsuji,10 has been converted by him to methyl dihydrojasmonate10 and 18-hydroxyestrone.11 Experimental Section General Methods. XH NMR spectra were determined on a JEOLCO MH-100 spectrometer as solutions in CDC13. Chemical shifts are reported in parts per million downfield from the internal reference tetramethylsilane. Couplings (J) are in hertz. The infrared spectra (IR) were recorded on a Perkin-Elmer 257 spectrometer as solutions in CC14 and are reported in reciprocal centimeters. Mass spectra were determined at 70 eV on an LKB 9000 gas chromatograph-mass spectrometer interfaced with a PDP-12 computer system and are reported as mass per unit charge, with intensities as a percentage of the peak of greatest ion current having m/z> 100 in parentheses. High-resolution mass spectroscopy was carried out on a VG 7070f double-focusing mass spectrometer. Organic chemicals were purchased from Aldrich Chemical Co. Organometallics were purchased from Alfa Inorganics and were titrated prior to use. Solvent mixtures (e.g., 5% ethyl acetate/hexane) are volume/volume mixtures. The Rf values indicated refer to thin-layer chromatography on Analtech 2.5 X 10 cm, 250-fim analytical plates coated with silica gel GF.Column chromatography was carried out by using TLC-mesh silica gel, following the procedure we have described.12 Preparation of 6.13 Diazo ester 1 (1.55 g, 5.50 mmol), prepared by alkylation of the dianion of methyl acetoacetate1 234 5followed by diazo transfer,5,6 was diluted with 30 mL of CH2C12 (dried by filtration through K2C03) under N2. Rhodium(II) acetate7 (0.040 g) was added, and the mixture stirred at room temperature for 30 min. Vigorous gas evolution was observed, and the solution turned a bright emerald green. The reaction mixture was diluted with 4% aqueous HC1 and extracted with CH2C12. The combined organic extracts were dried over Na2S04 and concentrated in vacuo.

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“…The plasmon resonance and large effective cross section of individual silver nanoparticles have significant potential for single molecule labeling-based biological assays [228,229,231]. Metal organosol should be a promising candidate especially for organic molecules from a homogeneity point of view [232].…”

Section: Surface-enhanced Raman Scattering Studymentioning

confidence: 99%