1- Ethoxy-4-nitrobenzene

To a solution of 2-(5-ethyl-2-pyridyl)ethanol (53.0 g) and 4-fluoronitrobenzene (47.0 g) in DMF (500 ml) was added portionwise under ice-cooling 60% sodium hydride in oil (16.0 g). The mixture was stirred under ice-cooling for one hour, then at room temperature for 30 min, poured into water and extracted with ether. The ether layer was washed with water and dried (MgS04). The solvent was evaporated off to give 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene as crystals (62.0 g, 62.9%). Recrystallization from ether-hexane gave colorless prisms, melting point 53°-54°C. 

A solution of 4-[2-(5-ethyl-2-pyridyl)ethoxy]nitrobenzene (60.0 g) in methanol (500 ml) was hydrogenated at room temperature under one atmospheric pressure in the presence of 10% Pd-C (50% wet, 6.0 g). The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residual oil was dissolved in acetone (500 ml)-methanol (200 ml). To the solution was added a 47% HBr aqueous solution (152 g). The mixture was cooled, to which was added dropwise a solution of NaN02 (17.3 g) in water (30 ml) at a temperature not higher than 5°C. The whole mixture was stirred at 5°C for 20 min, then methyl acrylate (112 g) was added thereto and the temperature was raised to 38°C. Cuprous oxide (2.0 g) was added to the mixture in small portions with vigorous stirring. The reaction mixture was stirred until nitrogen gas evolution ceased, and was concentrated under reduced pressure. The concentrate was made alkaline with concentrated aqueous ammonia, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried (MgS04) The solvent was evaporated off to leave methyl 2-bromo-3- 4-[2-(5-ethyl-2-pyridyl)ethoxy]phenyl propionate as a crude oil (74.09 g, 85.7%). 

C8H9NO3) E. Loss of a C H-i p-Ethoxy-nitrobenzene radical from metastable ions 140 g, n,p 481... 

Ethoxy nitrobenzene is prepared from ehlorobenzene by its nitration followed by treatment with sodium ethoxide, whieh on reduetion yields/(-phenetidine. The resulting product is diazotised with nitrous aeid at 0°C reaeted with phenol, ethyl bromide and reduced to obtain two moles of/(-phenetidine which upon acetylation with acetic anhydride yields two moles of phenacetin. 

Enolate generation, 106-7 Enolate trapping, 99-101 Enones, 34-5 Epoxidation, 21-3 a/3-Epoxysilanes, 21-4, 78 -Ethoxy acylsilane, 110 1-Ethoxy-l-trimethylsilyloxycyclo-propane,133 Ethyl bromoacetate, 123 Ethyl 2-chloropropanoate, 133 Ethyl glycinate, 87,88-9 Ethyl m-nitrobenzene, 137 Ethyl irimethylsilylacetate. 71, 123-4, 134 Ethyllithium, 66... 

Compounds with the structure 116 carrying ethoxy or methoxy groups in D-position are prepared from o-alkoxyanilines. Not only are cyclization and condensation achieved at comparatively lower temperature, between 170 and 175°C, but the reaction also proceeds at a higher rate than for compounds with D =H. One of the above-mentioned condensation agents is similarly necessary in this case. o-Dichlorobenzene, for instance, is a suitable organic solvent. The list of solvents for condensation and cyclization also includes trichlorobenzene and nitrobenzene. The reaction conditions are not markedly affected by the type of substitution in positions A and B. 

Direct preparation of azo compounds in good yields is accomplished by treatment of nitro compounds with lithium aluminum hydride [576], with magnesium aluminum hydride [577], with sodium bis(2-methoxy ethoxy)aluminum hydride [575], with silicon in alcoholic alkali [331] or with zinc in strongly alkaline medium [578], Hydrazobenzene was obtained by controlled hydrogenation of nitrobenzene in alkaline medium (yield 80%) [572] and by reduction with sodium bis 2-methoxyethoxy)alumium hydride (yield 37%) [544],... 

C8H9N03 1 -ethoxy-3-nitrobenzene 621-52-3 537.15 47.465 1,2 13869 C8H10N2O phenyl acetic acid hydrazide 937-39-3 506.65 44.523 2... 

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