Phthalimide 4-nitro

Nitro compounds. Nitromethane Nitrobenzene ni-Dinitrobenzene. Amides and imides. Acetamide re-Caproamide Acetanilide Benz-anilide Phthalimide. 

I itro-DisplacementPolymerization. The facile nucleophilic displacement of a nitro group on a phthalimide by an oxyanion has been used to prepare polyetherimides by heating bisphenoxides with bisnitrophthalimides (91). For example with 4,4 -dinitro monomers, a polymer with the Ultem backbone is prepared as follows (92). Because of the high reactivity of the nitro phthalimides, the polymerkation can be carried out at temperatures below 75°C. Relative reactivities are nitro compounds over halogens, Ai-aryl imides over A/-alkyl imides, and 3-substituents over 4-substituents. Solvents are usually dipolar aprotic Hquids such as dimethyl sulfoxide, and sometimes an aromatic Hquid is used, in addition. 

Propenylphenoxy compounds have attracted much research. BMI—propenylphenoxy copolymer properties can be tailored through modification of the backbone chemistry of the propenylphenoxy comonomer. Epoxy resins may react with propenylphenol (47,48) to provide functionalized epoxies that may be low or high molecular weight, Hquid or soHd, depending on the epoxy resin employed. Bis[3-(2-propenylphenoxy)phthalimides] have been synthesized from bis(3-rutrophthalimides) and o-propenylphenol sodium involving a nucleophilic nitro displacement reaction (49). They copolymerize with bismaleimide via Diels-Alder and provide temperature-resistant networks. 

The 4-nitro-A -phthalimide, prepared by heating the amine with the anhydride to 130° for 30 min, is cleaved with MeNHCH2CH2NH2 (71-92% yield). These cleavage conditions were compatible with cephalosporins, where the phthalim-ide was removed in 92% yield at —50° in 30 min. ... 

An isoindol1 none moiety forms part of the aromatic moiety of yet another antiinflammatory propionic acid derivative. Carboxylation of the anion from -nitro-ethylbenzene (45) leads directly to the propionic acid (46). Reduction of the nitro group followed by condensation of the resulting aniline (47) with phthalic anhydride affords the corresponding phthalimide (48). Treatment of that intermediate with zinc in acetic acid interestingly results in reduction of only one of the carbonyl groups to afford the isoindolone. There is thus obtained indoprofen (49). ... 

Primaquine Primaquine, 8-[(4-amino-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.4), is made from 6-methoxy-8-nitroquinoline (37.1.2.1), which is synthesized in a Skraup reaction from 4-methoxy-2-nitroaniline and glycerol in the presence of sulfuric acid. The nitro group in this compound is reduced to make 6-methoxy-8-aminoquinoline (37.1.2.2). Alkylating the amino group with 4-bromo-l-phthalimidopentane gives 8-[(4-phthalimido-l-methylbutyryl)amino]-6-methoxyquinoline (37.1.2.3), the hydrazi-nolysis of which removes the phthalimide protection, giving primaqnine [28,29]. 

Phases with phenyl groups are less retentive than C8 bonded phases. They show a pronounced selectivity and retention toward solutes with aromatic ring systems, attributed to n-n interactions. These n-n interactions can be improved when nitro substituted phenyl groups are bonded to silica. The strongest interactions have been reported with tetra nitro or tetra chloro phthalimide substituents. 

Sulfonsaure-alkylester konnen auch mittels Gabriel-Synthese in primare Amine iiber-gefuhrt werden. So lassen sich z, B. fluorierte Alkylamine wie 2-Amino-l,1,1-trifluor-ethan, 3-Amino-1,1,2,2-tetrafluor-propan und hohere Homologe durch Reaktion der entsprechen-den 2-Nitro-benzolsulfonsaure-fluoralkylester mit Kalium-phthalimid und anschliefiende Spaltung mit Hydrazin in guten Ausbeuten herstellen1. 

Polymerization via Nucleophilic Substitution Reaction. Halo- and nitro- groups attached to phthalimide groups are strongly activated toward nucleophilic substitution reactions. Thus polyetherimides are synthesized by the nucleophilic substitution reaction of bishaloimides (59,60) and bisnitroimides (61,62) with anhydrous bisphenol salts in dipolar aprotic solvents. 

N-[4-Nitro-2(or 3)-1rifluoromethyl-phenoxy]-EI6a/l 253 (Ar —Cl + N-OI1 phthalimid) N-(3-Oxo-4,4,4-trifluoro-l-butcnyl)-E10b, 537 (Educt) N-[4-Phenoxy-3-(lrifluoro-etheoyl)-plicnyl]- E10b, 564 (Educt)... 

Bromination (Br2) of 4,5,6,7-tetrahydrobenzo[6]thiophen-4-one affords either a 2-bromo or a 5-bromo derivative, depending on whether the reaction is carried out at 0° in ether,445,446 or at—5 to 0°in 50% aqueous acetic acid.354 The 5-bromo derivative condenses with morpholine or potassium phthalimide to give 140a or 140b, respectively.445, 446 Hydrazinolysis of 140b fails to give any of the 5-amino derivative.445,446 On nitration, the 2-bromo derivative affords the 3-nitro compound or 141 (R = N02), depending on the reaction conditions.354 With sodium azide in PPA the 2-bromo and 2-bromo-3-... 

Linder, W., N-Chloromethyl-4-nitro-phthalimide as a derivatizing reagent for HPLC, J. Chromatogr., 198, 367, 1980. 

Toluene-p- sulphon- amide °C Benzylidene derivative °C Picrate °C 3-Nitro- 2,4-Dinitro- Formyl Phenyl phthalimide phenyl derivative thiourea °C derivative °C °C °C ... 

Since the nitro-add corresponding to the o-amido benzene add is difficult to obtain, and phthalimide is easily prepared, the Hofmann reaction in this case gives a very convenient method of preparation for the amido-add. 

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