[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].S(OC)(O[CH3:24])(=O)=O>S(=O)(=O)(O)O.CN(C=O)C.O.C(O)(=O)C>[Br:1][C:2]1[C:3]2[C:11](=[O:13])[C:10]3[C:9](=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:8]([CH3:24])[C:4]=2[CH:5]=[CH:6][CH:7]=1(Method E-1) 2-(3-Bromo-phenylamino)benzoic acid, 13 (9.5 g, 32.5 mmol) was dissolved in conc. sulphuric acid (50 ml) and heated to 100° C. for 40 mins. After cooling, water was added slowly giving a green solid. The solid was filtered off and washed with water, and dried over phosphorous pentoxide. The crude material was partially dissolved in DMF (100 ml) and slowly added under nitrogen to sodium hydride (3.75 g, 156 mmol) in DMF (50 ml), and the mixture stirred for 30 mins. Dimethyl sulphate (12 ml, 72 mmol) was added and stirring continued for a further 30 mins before adding acetic acid (1 ml), then water (400 ml). The precipitate was filtered off, and the crude mix of 1 and 3-bromo acridones separated by column chromatography to give the title compound (2.43 g, 8.86 mmol, 26% over 2 steps). See, for example, Hodgeman et al., 1972.
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