Acridine nitration

Acridine and derivs 1 A94-A95 acridine dichromate 1 A95 acridine nitrate 1 A95 acridine perchlorate 1 A95 acridine picrate 1 A95 acridine-1,3,5-trinitrobenzene salt 1 A95 dinitroacridine 1 A94 mononitroacridine 1 A94... 

The nitration of acridine (9 R = H) in sulfuric acid is an unsatisfactory reaction in that the mixed isomers produced are difficult to separate. The main product is 2-nitroacridine (9 R = N02) the order of reactivity being 2>4>1>3 and product ratio 130 25 5 1 respectively (B-66MI20600). Acridine AT-oxide, however, undergoes nitration at 0°C to produce 9-nitroacridine AAoxide (10) (60JCS3367). 

Nofe Some nitrated acridines were first prepd by C.Graebe H.Caro, Ann 158,275-7(1871), who used warm nitric acid of d ca 1.45 as the nitrating medium. Formulas reptd by G C are not the same as given in Beil, Trinitroocridine, ClsH4N(NOa)3, mw 314.21,... 

Note C.Graebe H.Caro, Ann 158,277(1871) claimed the prepn of retranitroacridine by nitrating acridine with mixed nitric-sulfuric acid. Thecompd was in the form of reddish plates having N content 16. 38%. This compd did not appear to be tetranitroacridine. No refs to its expl props were made... 

Acridine Dichromate, (C HsN),. HsCraO orange-yel ndls was prepd in 1871 by treating a salt of acridine (such as nitrate) with KjCtjOj, Its structure was detd by Kahn(Ref 3)... 

Col crysts, mp 354° insol in w, si sol in ale or eth. It was first prepd in lS80(Ref 2) by treating acridine with chromic acid, but its identity was not established until 1892 (Ref 3). Its method of prepn by heating on a water bath N-phenylanthranilic acid with coned HaS04 is given in Ref 4. Can be nitrated to form nitrocompds Refs l)Beil 21,335,(312) [2801 2)C. 

Following are some refs on amino-acridine, aminoacridine nitrate and mono, di- trinitro-aminoacridine s... 

The situation regarding the nitration of acridines seems to be unclear. It has been said that nitration and chlorination of 9-phenylacridine (64a)... 

The nitrations of a wide range of substituted quinoline N-oxides under various conditions [82HC(382)447] show the usual pattern of substituent effects superimposed upon the pattern resulting from the use of nitric acid/sulfuric acid at low temperature (5,8-positions), weaker mixtures of these acids at high temperature (4-position), or acyl nitrates (3-position). Nitration of acridine N-oxide by nitric acid/sulfuric acid occurs in the 5-position (60JCS3367). 

Acridine 613, phenanthridine 614, cinnoline 615, and quinazoline 616 are nitrated as shown in Figure 3. 

Acridine, halogenation, 59, 295 Acridine A-oxide, halogenation, 59, 295 Acridine, 9-benzyl-, nitration, 58, 251 Acridine, 9-phenyl-, nitration, 58, 251 Acridin-9(10//)-ones, see Acridones Acridizinium ion, see... 

Figure 10, Heavy-atom effect on room-temperature phosphorescence of acridine (a) with silver nitrate (0,25M),...

The degree of ionization of acidic and basic antimicrobial agents depends on pH. Some compounds are active only in the unionized state (e.g., phenolics) whereas others are preferentially active as either the anion or cation. It therefore follows that the activity of a particular concentration of an agent will be enhanced at a pH that favors the formation of the active species. Thus, cationic antibacterials such as acridines and quaternary ammonium compounds are more active under alkaline conditions. Conversely, phenols and benzoic acid are more active in an acid medium. Chlorbutol is less active above pH 5 and unstable above pH 6. Phenylmercuric nitrate is only active at above pH 6 whereas thiomersal is more active under acid conditions. The sporicidal activity of glutaraldehyde is considerably enhanced under alkaline conditions whereas hypochlorites are virtually ineffective at above pH 8. 

Sodium alginate is incompatible with acridine derivatives, crystal violet, phenylmercuric acetate and nitrate, calcium salts, heavy metals, and ethanol in concentrations greater than 5%. Low concentrations of electrolytes cause an increase in viscosity but high electrolyte concentrations cause salting-out of sodium alginate salting-out occurs if more than 4% of sodium chloride is present. 

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