[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([N+:16]([O-])=O)=[CH:9][CH:10]=3)[C:5](=[O:19])[C:4]=2[CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:16][C:8]1[CH:9]=[CH:10][C:11]2[NH:12][C:13]3[C:4](=[CH:3][C:2]([NH2:1])=[CH:15][CH:14]=3)[C:5](=[O:19])[C:6]=2[CH:7]=1
See Bogert et al., 1930. To a stirred suspension of 2-amino-7-nitro-9(10H)-acridone 11 (22.5 g, 88.2 mmol) in ethanol was added, in one lot, a solution of sodium sulphide nonahydrate (94.5 g, 0.394 mol) and sodium hydroxide (37.5 g, 0.938 mol) in water (1.625 L). The mixture was refluxed with stirring for 16 hr. On cooling, saturated sodium bicarbonate solution (250 mL) was added and the total volume of the mixture reduced to 700 mL on a rotary evaporator. The flask was chilled in ice for 3 hr after which the product was collected on a glass sinter. The product was washed with water (4×200 mL) followed by ice-cold ethanol (2×100 mL), dry ether (2×100 mL) and finally hexane (2×100 mL). The product, 12, was dried over P2O5 under vacuum to yield an olive-green solid (18.70 g, 94%).
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