NaOEt

The toluene solution from the previous step was treated with an ethanol solution of NaOEt (0.1 mol in 100 ml) at O C. When about a quarter of the solution had been added a thick precipitate formed and ether (100 ml) was added to maintain a fluid slurry. The remainder of the NaOEt was added and the slurry was stirred overnight. The solid was collected and w ashed with ether. It was then mixed with ether (200 ml) and 2NHC1 (75 ml) and shaken in a separatory funnel until the solid dissolved. The ether layer was washed with 2NHHC1 (2 X 50ml) and water and dried over MgS04. The solution was decolorized with Magnesol and evaporated to give the a-nitro ester as a red oil. 

N-(4 Methoxyphenyl)-N-benzoyl-3-chloro-3-chloroantranlllc acid (4) 2 To ice cooled NaoEt (Irom 0 11 g Na and 10 mL ElOH) was added in rapid succession meltiyl 2 chloro 6 hydroxybenzoate 2 (0 86 g 4 7 mmol) and N (4 methoxyphenyl)benzimidyl chloride 1 (t 14 g 4 7 mmol) in EI2O (30 mL) The mixture was stirred vigorously and allowed to stand at rt tor 48 h The oily solid obtained alter evaporation was heated to 210 215°C lor 70 min under N2 The product was diluted with water (5 4 mL) ElOH (10 8 mL) and treated with 1 M NaOEt (5 4 mL) The mixture was relluxed lor 90 mm the solvent evaporated and the aqueous solution acldilied The dark oil was heated with NaOH (7 5 g) m EtOH (22 mL) Alter removal ol benzoic acid by exhaustive extraction with water the product was recrystallized Irom EtOH to give 0 36 g ol 4 (27 7%), mp 139 5 140 5°C... 

Hyponitrites can be prepared in variable (low) yields by several routes of which the commonest are reduction of aqueous nitrite solutions using sodium (or magnesium) amalgam, and condensation of organic nitrites with hydroxylamine in NaOEt/EtOH ... 

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