C([N:3](CC)CC)C.P(N=[N+]=[N-])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([CH:35]=[CH:36][CH:37]=1)C(O)=O.O>C1(C)C=CC=CC=1>[CH3:27][O:28][C:29]1[C:30]([N+:38]([O-:40])=[O:39])=[C:31]([NH2:3])[CH:35]=[CH:36][CH:37]=1Triethylamine (6.29 mL) and diphenyl azidophosphate (6.66 mL, 30.1 mmol) were added to a suspension of 3-methoxy-2-nitrobenzoic acid (3.00 g, 15.2 mmol) in toluene (50 mL). The reaction mixture was stirred under reflux for 2 hours, water (10 mL) was added and it was stirred overnight under reflux. After evaporation of the solvent, the residue was dissolved in AcOEt and the resulting solution was filtered through celite. The organic phase was washed with saturated solution of NaHCO3, brine, dried over MgSO4, filtered and evaporated. The crude residue was purified by flash chromatography (cyclohexane/AcOEt 4:1) to yield 900 mg (5.35 mmol, 35%) of 3-methoxy-2-nitrophenylamine as a yellow solid.
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