Phthalimide nitration

Dinitronitran ilinonitrophthalimide, C14H6NtO mw 418.24, N 20.10% Trinitroanilinonitro-phthalimide, CuH6N6O10,and higher nitrated derivs were not found in Beil or CA through 1956. If prepd, some would undoubtedly be explosive... 

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-... 

I. Care must be taken that the nitrating mixture is brought to 10-15° prior to the addition of the phthalimide. If a higher temperature is used, the reaction mixture tends to heat up spon-... 

Nitrophthalimide has been prepared from 4-nitrophthalic acid, and by nitrating phthalimide. The present procedure is a modification of the method of Levy and Stephen. ... 

Phthalimide behaves analogously further, the cyclic diamidine of phthalic acid (1,3-diiminoisoindoline) can be obtained in high yield by adding ammonium nitrate to a melt of the anhydride and urea 738... 

Nitrosophenylhydroxylamine ammonium salt Nonylphenol Nuarimol 2-n-Octyl-4-lsothlazolin-3-one Oleyl hydroxyethyl imidazoline Paraformaldehyde Pentachlorophenol Phenoxyacetic acid Phenylacetic acid Phenylmercuric borate Phenylmercuric nitrate Phenylmercuric oleate p-Phenylphenol Phthalimide... 

Two diphenylaminophthalides have been synthesized The 3,3-diphenyl-6-aminophthalide [24] was synthesized in 20% yield by the following sequence of reactions which was patterned after early work °. This series involved nitration of phthalimide, hydrolysis and dehydration to 4-nitrophthalic anhydride, Friedel-Crafts reaction with benzene to 2-benzoyl-5-nitrobenzoic acid, cyclization with thionyl chloride to the pseudoacid chloride, Friedel-Crafts reactions with benzene, and, finally reduction of the nitro group to the amino function with Adams catalyst. 

---