Cl.[CH3:2][NH:3][O:4][CH3:5].[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:8]=1[C:9](O)=[O:10].CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[NH2:6][C:7]1[C:15]([Cl:16])=[CH:14][CH:13]=[C:12]([Cl:17])[C:8]=1[C:9]([N:3]([O:4][CH3:5])[CH3:2])=[O:10]
N,O-dimethylhydroxylamine hydrochloride (3.28 g, 33 mmol) and 2-amino-3,6-dichlorobenzoic acid (4.76 g, 22 mmol) were dissolved in DMF (110 ml). N-methylmorpholine (9.99 g, 99 mmol) and HBTU (12.5 g, 33 mmol) were added and the reaction was stirred over night (r.t.). The reaction was poured onto water, extracted twice with diethyl ether. The combined organic layers were dried over sodium sulfate, filtered and the solvent was evaporated. The residue was crystallized with heptane and a little bit of diethyl ether. The filtrate was purified by column chromatography (heptane:ethyl acetate=1:1) to yield the product as an off-white solid (5.52 g, 100%).
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