Abstract
ON reduction by lithium aluminium hydride, amides usually give amines1: it has now been found that N-methyl phenanthridones behave rather differently, yielding quaternary (phenanthridinium) compounds. Phenanthridones are reduced to phenanthridines. Thus, N-methyl phenanthridone and N-3-dimethyl phenanthridone (m.p. 139°; found: C, 80.6; H, 5.8; N, 6.15 per cent; calc. for C15H13ON: C, 80.7; H, 5.8; N, 6.3 per cent) reduced in ethereal solution on the 300-mgm. scale gave respectively 60 and 55 per cent yields of the quaternary iodides (3-methyl phenanthridine methiodide, m.p. 278°; found: C, 53.8; H, 4.1; N, 4.5; I, 37.4 per cent; calc. for C15H14NI: C, 53.75; H, 4.2; N, 4.18; I, 37.9 per cent). The analogous N-methyl quinolone likewise gave N-methyl quinolinium chloride (identified as its platinichloride), but the reaction was less easy, two hours refluxing in dibutyl ether giving a 20 per cent yield. Among the reduction products of N-methyl pyridone, only a trace of quaternary compound (isolated as picrate) was found, together with methylamine (7 per cent isolated as the platinichloride).
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Nystrom and Brown, J. Amer. Chem. Soc., 70, 3738 (1948). Julian and Printy, J. Amer. Chem. Soc., 71, 3206 (1949). Uffer and Schlittler, Helv. Chim. Acta, 31, 1397 (1948).
Wooten and McKee, J. Amer. Chem. Soc., 71, 2946 (1949).
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DE MAYO, P., RIGBY, W. Reduction of some Cyclic Amides by Lithium Aluminium Hydride. Nature 166, 1075 (1950). https://doi.org/10.1038/1661075b0
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DOI: https://doi.org/10.1038/1661075b0
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