69628-96-2

Upstream product

• 15121-84-3 2-nitro-benzeneethanol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 677708-75-7 3-{4-[2-(2-Nitro-phenyl)-ethyl]-piperazin-1-yl}-1,2-benzisothiazole 
• 16968-19-7 2,2'-dinitrobibenzyl 
• 16793-89-8 (2-bromoethyl)-2-nitrobenzene 
• 650629-24-6 5'-(3-(2-aminophenyl)propionyl)-2'-deoxy-5-fluorouridine 
• 2001-32-3 3-(2-nitrophenyl)propionic acid 
• 114304-24-4 3-(2-nitrophenyl)propionitrile 
• 101562-80-5 1-Nitro-2-(2-thiomethoxyethyl)-benzene 

Relevant academic research and scientific papers

Synthesis of 2-(2-Methoxyethyl)- and 2-(2-Thiomethoxyethyl)-aniline and Related Compounds

2-(2-Nitrophenyl)-ethanol (2) was methylated with dimethyl sulfate to give 2-(2-methoxyethyl)-1-nitrobenzene (3a) which then was reduced with hydrazine hydrate in the presence of Raney nickel to 2-(2-methoxyethyl)-aniline (1a).Compound 1a can be transformed into the N-monosilylated derivative 4 by lithiation with n-butyllithium and subsequent reaction with chlorotrimethylsilane.Reaction of 2 with p-toluenesulfonyl chloride yields 2-(2-nitrophenyl)-ethyl p-toluenesulfonate (5), which reacts with sodium thiomethoxide to give 2-(2-thiomethoxyethyl)-1-nitrobenzene (3b). 3b was reduced with hydrazine hydrate in the presence of Raney nickel to yield 2-(2-thiomethoxyethyl)-aniline (1b).Ethyl (2-nitrophenyl)-acetate (6) could be dimethylated with methyl iodide in the presence of potassium tert-butoxide and 18-crown-6 to give ethyl 2-methyl-2-(2-nitrophenyl)-propionate (7).Reduction of 7 with lithium borohydride yields 2,3-dihydro-3,3-dimethyl-1H-indole (9) and 2--aniline (10). - Keywords: 2-Functionalized anilines; Hemilabile ligands; Imido ligands

Reduction of 1-(2-Chloroethyl)-2-nitrobenzene and 1-(2-Bromoethyl)-2- nitrobenzene at carbon cathodes: Electrosynthetic routes to 1-nitro-2- vinylbenzene and 1H -indole

Studies of the electrochemical reductions of 1-(2-chloroethyl)-2- nitrobenzene (1) and 1-(2-bromoethyl)-2-nitrobenzene (2) at carbon cathodes in dimethylformamide (DMF) containing tetramethylammonium tetrafluoroborate (TMABF4) have been undertaken. Cyclic voltammograms for 1 and 2 exhibit three irreversible cathodic peaks, the first of which is attributed to one-electron reduction of the nitro group, and the resulting nitro radical-anion immediately reacts as a base with the adjacent alkyl halide moiety via an E2 elimination to produce 1-nitro-2-vinylbenzene. At a potential corresponding to the first cathodic peak, bulk electrolyses of 1 or 2 in the absence of a proton donor afford 1-nitro-2-vinylbenzene as principal product, along with 1H -indole and a dimeric species. However, when 1 or 2 is electrolyzed in the presence of either phenol or 2,4-pentanedione as a proton source, the only significant product is 1H -indole. A mechanistic picture for the reductions of 1 and 2 is proposed, and a separate examination of the electrochemical behavior of 1-nitro-2-vinylbenzene has been included as part of this work.

Opioid ligands with mixed properties from substituted enantiomeric N-phenethyl-5-phenylmorphans. Synthesis of a -agonist δ-antagonist and δ-inverse agonists

Enantiomeric N-phenethyl-m-hydroxyphenylmorphans with various substituents in the ortho, meta or para positions of the aromatic ring in the phenethylamine side-chain (chloro, hydroxy, methoxy, nitro, methyl), as well as a pyridylethyl and a indolylethyl m

PHENYLALKYL AND PYRIDYLALKYL PIPERAZINE DERIVATIVES

This invention relates to compounds of the formula (1) wherein R1, R3, R4, X1, and X2 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system and other disorders.

Heterocyclic substituted piperazines for the treatment of schizophrenia

This invention relates to compounds of the formula 1 wherein Ar, A, R2, R3, Y and ring Q are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disord

5′-(2-Nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines as potential prodrugs of FUDR for reductive activation

Four 5′-(2-nitrophenylalkanoyl)-2′-deoxy-5-fluorouridines (1a-d) were designed and synthesized as potential prodrugs of FUDR for reductive activation. Two methyl groups were introduced α to the ester carbonyl to increase both the rate of cyclization activation and the stability of the conjugates towards serum esterases. Chemical reduction of the nitro group into an amino leads to cyclization and release of the active FUDR. Kinetic analysis of the cyclization activation process indicates that the two methyl groups α to the ester carbonyl restrict the rotational freedom of ground state molecule and promote the cyclization reaction. However, the two methyl groups also were found to render the conjugates as poor substrates of E. coli B nitroreductase. Conjugate 1c, without the two methyl groups, was reduced by E. coli B nitroreductase (t1/2=8 h) to give two products, a N-hydroxyl lactam and the drug FUDR, suggesting that the enzymatic reduction and subsequent cyclization activation proceeded through the hydroxylamine intermediate. These results indicate that cyclization activation will occur once the nitro group is reduced either to an amino or to a hydroxylamino group. The fact that the amino intermediates cyclized easily to release the incorporated drug FUDR suggests the feasibility of using peptide-linked acyl 2-aminophenylalkanoic acid esters as potential prodrugs for proteolytic activation.