Über den Mechanismus der Sauerstoffübertragung bei der Hydrierung von 2‐Nitro‐benzonitril zu 2‐Amino‐benzamid

Musso, Hans; Schröder, Hanna

doi:10.1002/cber.19650980532

Cited by 25 publications

(4 citation statements)

References 17 publications

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“…In the first one, the nitro group of 1 is reduced to the hydroxylamine 3, presumably via the corresponding nitrosoarene. This is supported by the fact that 2 ,2 '-dicyanoazoxybenzene [2 ] can be isolated after a change of the reaction con ditions (lower concentration of 1, 0.12 N acid, less negative potential of -5 0 -► -350 mV). Arylhydroxylamines are also reported as the first inter m ediates in the cathodic reduction of other orthosubstituted nitrobenzenes [3][4][5][6][7][8][9][10][11][12].…”

supporting

confidence: 51%

Electrosynthesis of 2-Alkyl-4(3H)-quinazolinones

Estrada

Rieker

1994

Zeitschrift Für Naturforschung B

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supporting

confidence: 51%

Electrosynthesis of 2-Alkyl-4(3H)-quinazolinones

Estrada

Rieker

1994

Zeitschrift Für Naturforschung B

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“…Most of the literature focuses on hydrogenation of 2-nitrobenzonitrile [1 -5]. RaNi [1,2], Pt [2,3,5], Pd [3 -5] and Ni [1] have been used as the catalysts and the most common solvent was alcohol (usually methanol or ethanol). The main product of this reaction was aminobenzamide (anthranilamide).…”

Section: Introductionmentioning

confidence: 99%

Hydrogenation of nitrobenzonitriles using Raney nickel catalyst

Koprivova

Červený

2008

Res. Chem. Intermed.

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Abstract-2-, 3-, 4-Nitrobenzonitriles were hydrogenated using Raney nickel catalyst in the environment of two different solvents (methanol and dioxane). The position of the nitro group relative to the nitrile group plays the dominant role in the course of hydrogenation. The nearer the substituent to the nitrile group is, the larger is its effect. 3-and 4-nitrobenzonitriles were hydrogenated to their primary amines, in contrast to 2-nitrobenzonitrile, which was transformed via intramolecular oxidation to 2-aminobenzamide. During hydrogenation, numerous intermediates were formed. The choice of the solvent is another significant parameter affecting the course of hydrogenation.

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“…Bromination (9) of 2,3-dimethyl-1-nitrobenzene (20) gave 2-bromomethyl-3-dibromomethyl-1-nitrobenzene (21), which on treatment (9) with sodium iodide in N,N-dimethylformamide and fumaronitrile (22) yielded the known 5-iodo-2,3-dicyanonaphthalene (23), prepared by a different route (26). Reduction of 23 (26), gave 5-amino-2,3-dicyanonaphthalene (24) (26), which upon diazotization and treatment with potassium iodide gave the unknown 5-iodonaphthalene-2,3-dicarbonitrile (25).…”

Section: Bisdicyanoarylethenes From Dicyanoiodoarenesmentioning

confidence: 99%

“…The selective reduction of 13 was facilitated using a poisoned catalyst (22,23). A mixture of 2.5 g of 5% palladium on barium sulfate and 5 mg of thiourea in 2.5 mL of methanol was shaken for 1 h. The solvent was evaporated and the brown residue homogenized.…”

Section: -Ai~ziizophthaloizitrile (14)mentioning

confidence: 99%

Multisubstituted phthalonitriles, naphthalenedicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanine syntheses

Leznoff¹,

Terekhov²,

McArthur³

et al. 1995

Can. J. Chem.

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Electrophilic aromatic nitration under mild conditions of 4-hydroxyphthalonitrile gave 4-hydroxy-3-nitrophthalonitrile and 4-hydroxy-5-nitrophthalonitrile, while bromination yielded 3-bromo-4-hydroxyphthalonitrile, 4-bromo-5-hydroxyphthalonitrile, and 3,5-dibromo-4-hydroxyphthalonitrile. Iodination gave 4-hydroxy-5-iodophthalonitrile and 4-hydroxy-3.5-diidophthalonitrile. Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1.2-bis(tri-n-buty1stannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-I ,2-bis(2,3-dicyanophenyl)ethene, and trans-l,2-bis(6,7-dicyanonaphthy1)ethene. Photocyclization of a dilute solution of cis-or trans-I,2-bis(3,4-dicyanopheny1)ethene in dioxane gave a 1: 1 mixture of 2,3,6,7-and 2,3,5,6-tetracyanophenanthrenes separable by chromatography.Key words: phthalonitriles, naphthalenedicarbonitriles, phenanthrenetetracarbonitriles, electrophilic substitution.Resume : La nitration Clectrophile aromatique du 4-hydroxyphtalonitrile, dans des conditions douces, conduit au 4-hydroxy-3-nitrophtalonitrile et au 4-hydroxy-5-nitrophtalonitrile alors que sa bromation fournit du 3-bromo-4-hydroxyphtalonitrile, du 4-bromo-5-hydroxyphtalonitrile, etdu3,5-dibromo-4-hydroxyphtalonitrile. L'iodation foumit du 4-hydroxy-5-iodophtalonitrile et du 4-hydroxy-3.5-diiodophtalonitrile. Le couplage des 4-iodophtalonitrile 3-iodophtalonitrile et 5-iodo-2,3-dicyanonaphtalkne avec du trans-l,2-bis(tri-11-butylstannyl)Cthkne fournit du trans-l,2-bis(3,4-dicyanophCnyl)6thkne, du trans-I ,2-bis(2,3-dicyanophCny1)Cthkne et du trans-1.2-bis(6,7-dicyanonaphty1)Cthkne. La photocyclisation d'une solution diluCe des isomkres cis-et trans-l,2-bis(3,4-dicyanophCny1)tthkne dans le dioxane fournit un melange I : 1 des 2,3,6.7-et 2.3.5.6-tCtracyanophCnanthrknes que l'on peut separer par chromatographie.

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Über den Mechanismus der Sauerstoffübertragung bei der Hydrierung von 2‐Nitro‐benzonitril zu 2‐Amino‐benzamid

Cited by 25 publications

References 17 publications

Electrosynthesis of 2-Alkyl-4(3H)-quinazolinones

Electrosynthesis of 2-Alkyl-4(3H)-quinazolinones

Hydrogenation of nitrobenzonitriles using Raney nickel catalyst

Multisubstituted phthalonitriles, naphthalenedicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanine syntheses

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