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Organic Lab Reactions 287

Organic Lab Reactions 287 - 4 The method is simple in...

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282 THE AROMATIC PRIMARY AMINO GROUP powder, gives phenanthrene in 80% yield. 66 Ethanol also yields phe- nanthrene instead of cts-stilbene. 66 ' * With the trans isomer, the Pschorr reaction is not possible; conversion to the stilbene takes place whether ethanol or hypophosphorous acid is employed. 66 Deamination of 4,5-dimethyl-8-aminoquinoline by hypophosphorous acid gives only a 6% yield of 4,5-dimethylquinoline. There is some evi- dence, however, that the diazotization takes an abnormal course. 84 In hypophosphorous acid reductions varying amounts of phenols and tars are obtained. In general, however, no difficulty is experienced in isolating products of excellent quality. REDUCTION WITH ALKALINE FORMALDEHYDE The reduction of diazonium salts by alkaline formaldehyde affords good yields of deaminated products in a number of instances.
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Unformatted text preview: 4 The method is simple in practice, and it is particularly effective where the ethyl alcohol procedure is of little or no value. Although there are com-paratively few examples of deaminations employing alkaline formalde-hyde, several generalizations can be made. Aromatic amines and their homologs are converted to the correspond-ing hydrocarbons in 60-80% yields; with alkoxy- and aryloxy-amines, the yields range from 50 to 75%. 4 The deaminations of 2,4-dimethyl-* It would be of interest to attempt this reduction under somewhat modified conditions; deamination might be achieved by treating the diazonium chloride with hypophosphorous aoid at 0° to +5° in the absence of copper....
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