[CH3:1][C:2]1([CH3:13])[C:6](=[N:7]N)[C:5](=[N:9][OH:10])[C:4]([CH3:12])([CH3:11])[O:3]1.Cl.N[OH:16]>O>[CH3:1][C:2]1([CH3:13])[C:6](=[N:7][OH:16])[C:5](=[N:9][OH:10])[C:4]([CH3:12])([CH3:11])[O:3]110.0 g (54 mmol) of commercially available 2,2,5,5-tetramethyl-3,4-(2H, 5H)-furandione hydrazone oxime are heated under reflux for 2 hours with 75 g (1.1 mmol) of hydroxylamine hydrochloride in 800 ml of water. The precipitated product is filtered off with suction and washed with water. 8 g (86%) of 2,2,5,5-tetramethyl-3,4(2H, 5H)-furandione dioxime are obtained as a mixture of 2 isomers, m.p. 252° C.
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