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Acetanilides nitration

On acetylation it gives acetanilide. Nitrated with some decomposition to a mixture of 2-and 4-nitroanilines. It is basic and gives water-soluble salts with mineral acids. Heating aniline sulphate at 190 C gives sulphanilic add. When heated with alkyl chlorides or aliphatic alcohols mono- and di-alkyl derivatives are obtained, e.g. dimethylaniline. Treatment with trichloroethylene gives phenylglycine. With glycerol and sulphuric acid (Skraup s reaction) quinoline is obtained, while quinaldine can be prepared by the reaction between aniline, paraldehyde and hydrochloric acid. [Pg.35]

Mono-substitution products of primary amines cannot easUy be prepared by direct action of the appropriate reagent for example, bromination of aniline yields largely the 2 4 6-tribomo derivative and nitration results in much oxidation. If, however, the amino group is protected as in acetanilide, smooth substitution occurs. Thus with bromine, />-bromoacetanilide is the main product the small quantity of the ortlio isomeride simultaneously formed can be easily eliminated by crystallisation. Hydrolysis of p-bromoacetanilide gives/ -bromoaniline ... [Pg.577]

Without further studies little weight can be given to these ideas. In particular there is the possibility that with acetanilide, as with anisole, nitrosation is of some importance, and further with nitrations in sulphuric acid the effect of protonation of the substrate needs quantitative evaluation. The possibility that the latter factor may be important has been recognised, and it may account for the difference between nitration in sulphuric acid and nitration with nitronium tetrafluoroborate. [Pg.96]

TABLE 5.6 Proportions of isomers formed in the nitration of acetanilide ... [Pg.97]

Other substituents which belong with this group have already been discussed. These include phenol, anisole and compounds related to it ( 5.3.4 the only kinetic data for anisole are for nitration at the encounter rate in sulphuric acid, and with acetyl nitrate in acetic anhydride see 2.5 and 5.3.3, respectively), and acetanilide ( 5.3.4). The cations PhSMe2+, PhSeMe2+, and PhaO+ have also been discussed ( 9.1.2). Amino groups are prevented from showing their character ( — 7 +717) in nitration because conditions enforce reaction through the protonated forms ( 9.1.2). [Pg.182]

Nitration. Direct nitration of aromatic amines with nitric acid is not a satisfactory method, because the amino group is susceptible to oxidation. The amino group can be protected by acetylation, and the acetylamino derivative is then used in the nitration step. Nitration of acetanilide in sulfuric acid yields the 4-nitro compound that is hydroly2ed to -rutroaruline [100-01-6]. [Pg.231]

Samal et al. [25] reported that Ce(IV) ion coupled with an amide, such as thioacetamide, succinamide, acetamide, and formamide, could initiate acrylonitrile (AN) polymerization in aqueous solution. Feng et al. [3] for the first time thoroughly investigated the structural effect of amide on AAM polymerization using Ce(IV) ion, ceric ammonium nitrate (CAN) as an initiator. They found that only acetanilide (AA) and formanilide (FA) promote the polymerization and remarkably enhance Rp. The others such as formamide, N,N-dimethylformamide (DMF), N-butylacetamide, and N-cyclohexylacetamide only slightly affect the rate of polymerization. This can be shown by the relative rate (/ r), i.e., the rate of AAM polymerization initiated with ceric ion-amide divided by the rate of polymerization initiated with ceric ion alone. Rr for CAN-anilide system is approximately 2.5, and the others range from 1.04-1.11. [Pg.542]

The Na salt of MEDINA was fluorinated in w, the sain extd with methylene chloride, and the solv evapd to give a yellow oil whose IR spectrum showed absence of NH and the presence of NF absorption, and analysis indicated was a mixt (Ref 22). Nitramines in the presence of sulfuric acid are capable of nitrating reactive aromatic compds, but when acetanilide was treated with MEDINA in the presence of this acid, no nitroacetanilide was isolated. Instead compds indicating that the MEDINA had been fragmented and the fragments reacted with the acetanilide were isolated (Ref 12)... [Pg.69]

To get a complex set of substituents by direct derivatization of benzotriazole is not feasible. In such situations, it is better to have all the substituents in place first and later construct the heterocyclic ring. High reactivity of anilines and their well-developed chemistry makes them good stating materials. In an example shown in Scheme 215, acetanilide 1288 is nitrated to afford nitro derivative 1289 in 73% yield. Catalytic reduction of the nitro group provides methyl 4-acetylamino-3-amino-5-chloro-2-methoxybenzoate 1290 in 96% yield. Nitrosation of compound 1290 in diluted sulfuric acid leads to intermediate 1291, which without separation is heated to be converted to 7-chloro-4-methoxy-l//-benzotriazole-5-carboxylic acid 1292, isolated in 64% yield <2002CPB941>. [Pg.144]

A change in ionic adsorption in the presence of organic molecules was also observed by Parsons and Zobel. They found that in the presence of acetanilide in the inner layer, the surface concentration of specifically adsorbed phosphate ions decreases. In another work it was suggested that specific adsorption of nitrate ions is markedly reduced in the presence of thiourea in the solution. Thiourea alters the properties of the mercury electrode, affecting even the adsorption of iodides. ... [Pg.55]

Solutions of sodium or potassium nitrates in concentrated sulfuric acid can be used as a substitute for anhydrous mixed acid." 2,4,6-Trinitroaniline (picramide) has been synthesized via the addition of a solution of potassium nitrate in concentrated sulfuric acid to a solution of either o- or p-acetanilide in oleum. ... [Pg.142]

Dinitw4 etbyl l metbyl benzener CH CcH CaHB(NOa)3 mw 210.20, N13.33% yel crysts, mp 48.5° Prepd from 5-ethyl 2 methyl-acetanilide by nitration at -1Q8-mp 177-8°, hydrolysis to the aniline-mp 186° followed by diazotization/removal of the amino group... [Pg.183]

A freshly prepared solution of nitroguanidine in sulphuric acid contains no free nitric acid, but in the presence of substances which are readily nitrated it behaves as if this were so, e.g. the solution nitrates phenol, acetanilide and cinnamic acid and in the presence of mercury reacts in a nitrometer with the evolution of nitric oxide in the same way as nitric acid. Hence in certain cases a solution of nitroguanidine in sulphuric acid may be utilized as a nitrating mixture. [Pg.26]

Note According to one of the Hercules Co Laboratory manuals, acetanilide was used as one of the ingredients of smokeless pro-pe Hants. Some nitrated acetanilide derivatives are explosive... [Pg.23]

Note nitration of acetanilide has been discussed in the following refs ... [Pg.23]

Note No nitrated derivs of acetyl-dl-alanine were found in Beil or CA through 1956 Acetylaniline. See Acetanilide... [Pg.54]


See other pages where Acetanilides nitration is mentioned: [Pg.14]    [Pg.243]    [Pg.245]    [Pg.14]    [Pg.14]    [Pg.243]    [Pg.245]    [Pg.14]    [Pg.108]    [Pg.167]    [Pg.168]    [Pg.94]    [Pg.96]    [Pg.199]    [Pg.205]    [Pg.239]    [Pg.3]    [Pg.697]    [Pg.672]    [Pg.142]    [Pg.172]    [Pg.138]    [Pg.313]    [Pg.205]    [Pg.523]    [Pg.23]   
See also in sourсe #XX -- [ Pg.262 ]

See also in sourсe #XX -- [ Pg.262 ]

See also in sourсe #XX -- [ Pg.66 , Pg.67 , Pg.72 ]

See also in sourсe #XX -- [ Pg.262 ]

See also in sourсe #XX -- [ Pg.267 ]

See also in sourсe #XX -- [ Pg.243 ]

See also in sourсe #XX -- [ Pg.716 ]




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Acetanilid

Acetanilide

Acetanilide preparation and nitration

Acetanilide, hydrolysis nitration

Acetanilide, nitration preparation

Acetanilide, nitration rearrangement

Acetanilide: bromination nitration

Ethyl acetanilide, nitration

Methyl acetanilide, nitration

Nitration of acetanilide

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