W Nitrobenzoyl chloride

Thus, acylation of 3(W,iV-dibutylamino)propanol (39) with p-nitrobenzoyl chloride affords the intermediate, 40. Reduction of the nitro group gives butacaine (41), an agent equipotent as cocaine as a topical anesthetic. 

Nitrobenzoyl peroxide,2 as well as w-nitrobenzoyl peroxide2 and anisoyl peroxide,3 have been prepared in about 50 per cent yields from the acid chlorides and an acetone solution of hydrogen peroxide, in the presence of a basic substance such as pyridine, sodium acetate, or sodium hydroxide. w-Nitrobenzoyl peroxide has also been prepared by nitration of benzoyl peroxide with cold... 

H (1947) (Hazards from chlorates perchlorates in admixtures) 43)May Baker Ltd, Chem Ind 1946, 89 CA 40, 2985 (1946) (Hazards in handling o-Nitro aromatic compds) 44)W. A.Bonner C.D.Hurd, JACS 68, 344-45 (1946) (Hazard involved in distillation of o-Nitrobenzoyl chloride) 45)W.G.Bailey A.Roy, JSCI 65, 421-22 (1946)... 

There are different methods of the synthetic preparation of acronycine (W. M. Bandaranayake et al., J. Chem. Soc. Perkin 1, 998 (1968) J. Hlubucek et al. Aust. J. Chem. 23, 1881 (1970). One of them is described below. Friedel-Crafts condensation between 2-nitrobenzoyl chloride and 3,5-dimethoxyphenol. 

Closely related to the anionic complexes described above are the neutral species [Cp2M(CO)H] (M = Nb or Ta), also capable of reducing acyl chlorides to aldehydes. The reactions are reported to be virtually instantaneous, and the reagents appear to have useful selectivity. For example, p-nitrobenzoyl chloride and cinnamoyl chloride are reduced to their corresponding aldehydes (although yields are not recorded). However, as with the Cr, W and V anionic hydrides, these neutral complexes may prove too inaccessible to be generally useful. 

A 10%-soln. of pentane-2,4-dione copper complex in chloroform shaken 12-24 hrs. at room temp, with a 10%-soln. of m-nitrobenzoyl chloride in the same solvent, and the crude intermediate triketone heated 10-15 min. with aq. 3 N NHg l-m-nitrophenylbutane-l,3-dione. Y 92%.—The method is simple, gives good yields of pure products, and is the most convenient one for the prepn. of certain / -diketones. F. e., also deacetylation of the triketones with ethanolic 30%-H2S04, and condensations with ethyl acetoacetate copper complex, s. W. J. Barry, Soc. 1960, 670. 

The procedure described for the preparation of l-(m-nitro-phenyl)-3,3-dimethyltriazene is the method of Elks and Hey,2 and the preparation of m-nitrobiphenyl is also a modification of their procedure. The other principal methods for the preparation of m-nitrobiphenyl are the decomposition of N-nitroso-w-nitroacetanilide in benzene 3 and the decomposition of alkaline m-nitrobenzenediazohydroxide in benzene.4 Other methods that have been reported include the decomposition of potassium ire-nitrobenzenediazotate in benzene with acetyl chloride,6 the decomposition of m-nitrobenzoyl peroxide in boiling benzene,6 the decomposition of benzenediazonium borofluoride in nitrobenzene 7 at 70°, and the reduction of 4-(3 -nitrophenyl)-benzenediazonium acid sulfate in boiling ethanol.8... 

By a procedure similar to that described for />-nitrobenzoyl peroxide, the following peroxides have been prepared w-nitro-benzoyl peroxide (m.p. 136-137°) in 90 per cent yield anisoyl peroxide (m.p. 126-127°) in 86-89 per cent yields -bromoben-zoyl peroxide (m.p. 144°) in 73 per cent yield and 3,4,5-tribromo-benzoyl peroxide (m.p. 186°) in 40 per cent yield.1 The procedure is not satisfactory for preparation of acetylsalicylyl peroxide, which is more conveniently prepared by action of hydrogen peroxide upon an acetone solution of the acid chloride. 

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