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Organic Lab Reactions 280

Organic Lab Reactions 280 - N 2 HSO 4-NO 2...

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INFLUENCE OF WATER NH 2 N 2 275 An extensive study of the methoxypolynitroanilines has shown that, in this series, a nitro or methoxyl group becomes sufficiently mobile to be eliminated during the course of diazotization only when ortho or para to the diazo group and, in addition, adjacent to a nitro group. 60 Picramide is diazotized by treating a solution of the amine in.glacial acetic acid with nitrosylsulfuric acid (prepared by dissolving sodium nitrite in concentrated sulfuric acid). 61 Addition of ice-cold water to the diazonium solution results in immediate decomposition of the diazonium salt. 61 - 62 - * ' Nitronaphthalenediazonium salts are more susceptible of hydrolytic cleavage than the corresponding benzenoid compounds. The elimination of a nitro group from 2,4-dinitrobenzene-l-diazonium acid sulfate is not effected merely by dilution with water, whereas it readily occurs with 2,4-dinitronaphthalene-l-diazonium acid sulfate. 36166 Because the dia- zonium salts are unstable in the presence of water, the deamination of N 2 +HSO 4 - NO 2 2-nitronaphthylamine-l
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Unformatted text preview: N 2 +HSO 4-NO 2 2-nitronaphthylamine-l and 2,4-dinitronaphthylamine-l requires diazo-tization with nitrosylsulfuric acid, followed by direct decomposition with ethanol. 36 Diazonium salts derived from nitro-/3-naphthylamines also undergo hydrolysis, and again it is an ortho nitro group that is removed. Thus, * The nature of the degradation products has not been established. Misslin implies (reference 61) that the 2-hydroxy-4,6-dinitrobenzenediazonium ion is produced, a view that is accepted by Karrer, "Organic Chemistry," p. 432, Nordemann Publishing Co., New York, 1938. There does not appear to be any experimental basis for this deduction, and in the light of Blangey's results (reference 62) the course of the reaction must be regarded as an open question. 60 Meldola and Hay, J. Chem. Soc, 91, 1474 (1907). 61 Misslin, Hdv. Chim. Ada, 3, 626 (1920). ! 82 Blangey, Helv. Chim. Ada, 8, 780 (1925)....
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