[H-].[Na+].[C:3]([O:10][CH2:11][CH3:12])(=[O:9])[C:4]([O:6]CC)=O.[C:13]1(=[O:25])[C:23]2=[C:24]3[C:19](=[CH:20][CH:21]=[CH:22]2)[CH2:18][CH2:17][CH2:16][CH:15]3[CH2:14]1.Cl>O1CCOCC1>[C:4]([CH:14]1[CH:15]2[C:24]3[C:19]([CH2:18][CH2:17][CH2:16]2)=[CH:20][CH:21]=[CH:22][C:23]=3[C:13]1=[O:25])([C:3]([O:10][CH2:11][CH3:12])=[O:9])=[O:6]To a suspension of 50% sodium hydride (7.4 g) in anhydrous dioxane (50 ml), under nitrogen, a solution of diethyl oxalate (34.5 g) in anhydrous dioxane (20 ml) and then a solution of 2a,3,4,5-tetrahydro-acenaphthen-1-one (20.4 g) in anhydrous dioxane (130 ml) are added under stirring at room temperature. The reaction mixture is kept under stirring at a temperature varying between about 25° C. and about 45° C. for 4 hours, then it is diluted with ice water (1500 ml) and acidified to pH 4 with 2N HCl. The precipitate is filtered, washed with water and then purified by treatment with methanol to give 2-ethoxalyl-2a,3,4,5-tetrahydro-acenaphthen-1-one (30.8 g), m.p. 92°-94° C., wich is reacted with methylhydrazine (5.7 g) in acetic acid (300 ml) at 50° C. for 1 hour.
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