Nitration of quinoline (I) with acid mixture gives 5-and 8-nitro compounds. In the case of 1, 2, 3, 4-tetrahydroacridine (II), 2, 3-dihydro-1
H-cyclopenta [
b] quinoline (III), 7, 8, 9, 10-tetrahydrophenanthridine (IV), and 2, 3-dihydro-1
H-cyclopenta [
c] quinoline (V), the nitration occurs in the position corresponding to 5-and 8-positions in I, i.e. 8- and 5-positions in II and III, 1-and 4-positions in IV, and 9-and 6-positions in V. In all of these compounds, it is difficult to make complete separation of the two kinds of nitrated compounds formed and therefore, their formation ratio is not clear. The 8-nitro compound (VI) of II, 8-nitro compound (XIII) of III, 1-nitro compound (XVI) of IV, and 9-nitro compound (XIX) of V can be derived to their corresponding N-oxides (XII, XV, XVIII, and (XXI) by treatment with monoperphthalic acid, but not the 5-nitro compound (VII) of II, 5-nitro compound (XIV) of III, 4-nitro compound (XVII) of IV, and 6-nitro compound (XX) of V, possibly because of the steric hindrance of the nitro group in the position peri to the ring nitrogen. The substance of m.p. 138-139° obtained by Borsche by nitration of II is probably VI, but the substance of m.p. 110° obtained by Perkin and others from II is doubtful about its being a unit substance, and may be a mixture of VI and VII. The substance of m.p. 119-120°, obtained by Hollingsworth and others and presumed by them to be XIV, may also be a mixture of XVI and XVII, and not a unit substance.
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