Erdmann reaction

The Husemann and Erdmann identification reactions for morphine and codeine in the DAB 9 (German Pharmacopoeia) involve the formation of the red-colored ortho-quinone (8) via apomorphine (5) under the influence of nitric acid with the simultaneous nitration of the benzene ring [15]. 

There is a conflict of opinion as to the manner in which the reaction takes place. Many investigators4 favour the view that the oxides only behave catalytically when they contain a certain amount of free, unoxidised metal, which suggests that it is the element itself and not the oxides which behave catalytically. Bedford and Erdmann, on the other hand, believe that no reduction to metallic nickel takes place during hydrogenation, and that when the higher oxides are used they become partially reduced to the suboxide, which forms a colloidal suspension in the oil. 

Either Erdmann s method, based on the reaction between... 

The reaction of ammonia on benzoin described by Erdmann was reinvestigated by Japp and Wilson (12) and Japp and Burton (13) and the product, tetraphenyl-pyrazine, renamed ditolanazotide and tetraphenylazine, respectively. 

This reaction was first applied by Erdmann (11) to the preparation of tetra-phenylpyrazine by heating benzoin (PhCHOHCOPh) with ammonia. The reaction of benzoin with ammonium acetate in glacial acetic acid has been investigated by Davidson et al. (257), and it has been shown that identical results were obtained when the benzoin was replaced by desylamine (PhCHNH2COPh). 

Erdmann S, Hertl M, Merk HF. Contact dermatitis from clotrimazole with positive patch-test reactions also to croco-nazole and itraconazole. Contact Dermatitis 1999 40(l) 47-8. 

Erdmann S, Roos T, Merk HF, Grussendorf-Conen Eli, Rubben A, Dahl T. Delayed hypersensitivity reaction to the non-ionic contrast medium ioversol. H G Z Hautkr 2000 75 169-71. 

N. Alonso-Vante, M. Fieber-Erdmann, H. Rossner, E. Holub-Krappe, C. Giorgetti, A. Tadjeddine, E. Dartyge, A. Fontaine, R. Frahm, The catalytic centre of transition metal chalcogenides vis-a-vis the oxygen reduction reaction An in situ electrochemical EXAFS study. J. de Physique IV France 1997, 7, C2-887-C2-889. 

NH NO, mw 64.04, N 43.74%. Wh to yel ndl-like deliquescent ctysts, d 1.69, mp — starts to sublime at 32—3° and decomp explosively >60° fl p 158°F. Readily sol in w(with evoln of heat) sol in ale and nearly insol in eth, chlf or ethyl acetate. Was first prepd in 1812 by J.J.Berzelius by treating Pb nitrite with Amm sulfate or by treating Ag nitrite with Amm chloride. Later, 1874, M.Berthelot used the reaction betw Ba nitrite and Amm sulfate and also the interaction of ammonia with nitric oxide and oxygen. O.L. Erdmann S.P.Sdrensen prepd it by passing a mixt of nitrogen oxides(obrained by the action of arsenic trioxide on nitric acid) over coarsely ground Amm carbonate, kept cool by ice the half liq mass was treated with ale, the unchanged carbonate filtered off and the Amm nitrite precipitated by the addn of ether. The nitrite so obtained... 

A step further in the utilization of these solvent-extracted compounds is their use as reagents. Irving and co-workers (8, 16) have reported what they call a colored liquid anion exchanger based on this concept. They use a xylene-hexone solution of tetrahexylammonium erdmannate. Erdmannate ion is the yellow [Co(NH3)2(N02)4] anion, which absorbs strongly at 353 m/x in aqueous solution. The exchange reaction is... 

Triamminetrinitrocobalt(III)> tCo(N02)j(NH3)3], was first prepar in 1866 by Erdmann, later by Werner and Jorgensen, who prepared the complex by the air-oxidation of ammoniacal cobalt(II) salt solutions containing sodiiun nitrite and a large amount of ammonium chloride. In 1938, Duval examined the products obtained from several different procedures by absorption and infrared spectroscopy, refractive index of aqueous solutions, conductivity, and X-ray powder diffraction. He recognized two products in the Werner s preparation and the Jorgensen s preparation. In that year, Sueda reported an isomeric complex from the reaction of the [Co(N03)j(NH3)3] complex with sodium nitrite in a cold aqueous solution, which was assumed to be cis-cis isomer on the basis of the absorption spectrum. 

In 1899, Erdmann obtained the same compound in good yield from anthranilic acid and phosgene and suggested the name isatoic anhydride. An alternative synthesis of isatoic anhydride [2//-3,l-benzoxazine-2,4(lH)-dione, subsequently abbreviated as lA] was found by Curtius and Semper from phthalic acid monoazide (5) via o-carboxyphenyl isocyanate. Similar rearrangements were discovered by Bredt and Hor [from potassium phthal-imide (6)] and by Mohr [from phthalimide (7)] leading to IA via a Hoffmann reaction. 

This reaction is related to the Bogert-Herrera Reaction and Volhard-Erdmann Cyclization ... 

Alonso-Vante N, Fieber-Erdmann M, Rossner H, Holub-Krappe E, Giorgetti C, Tadjeddine A, Dartyge E, Fontaine A, Frahm R (1997) The catalytic centre of transition metal chalcogenides vis-4-vis the oxygen reduction reaction an in situ electrochemical EXAFS study. J Phys IV 7(2 Part 2) 887-889... 

Erdmann (see Volhard-Erdmann Cyclization) Erlenmeyer-Plochl Azlactone and Amino Acid Synthesis Eschenmoser Coupling Reaction Eschenmoser Fragmentation Eschenmoser-Claisen Rearrangement Eschenmoser-Tanabe Fragmentation Eschweiler-Clarke Reaction Etard Reaction... 

Bachmann F, Erdmann R, Hartmann V, Becker-Wegerich P, Wiest L, Rzany B. Adverse reactions caused by consecutive irqections of different fillers in the same facial region risk assessment based on the results from the Irqectable Filler Safety study. J Eur Acad Dermatol Venereol 2011 25(8) 902-12. 

Salicylic acid-derived poly(anhydride-esters) using a benzyl protected salicylic acid and sebacoyl chloride in a coupling reaction with sodium hydride in tetrahydrofuran (Erdmann and Uhrich, 2000). 

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