[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[CH:6][C:4]=1[NH2:5].C(=O)(O)[O-].[Na+].[Cl:17][CH2:18][C:19](Cl)=[O:20]>O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:17][CH2:18][C:19]([NH:5][C:4]1[CH:6]=[C:7]([O:10][CH3:11])[CH:8]=[CH:9][C:3]=1[O:2][CH3:1])=[O:20]2,5-dimethoxyaniline (20 g., 130.56 mmol) was suspended in water (300 ml) followed by the addition of sodium bicarbonate (13.4 g., 156.6 mmol)) and tetrabutylammonium bromide (catalytic amount). To the mixture was added chloroacetyl chloride (12.4 ml, 156.6 mmol) dropwise at 0° C. The reaction mixture was stirred at room temperature for 1 h. The solid suspension was filtered off to yield pure 46. Yield=23.6 g (79%). 1H NMR: 9.46 (1H), 7.68 (1H, d, J=2.96 Hz), 6.96 (1H, d, J=8.96 Hz), 6.43 (1H, dd, J=8.95 and 3.06 Hz), 4.37 (s, 2H), 3.79 (s, 3H), 3.67 (s, 3H). 13C NMR: 43.3, 55.9, 56.2, 106.0, 111.0, 127.4, 127.7, 142.7, 154.0, 163.8. ES-HRMS [M+H]+ 230.0509. Calcd for (C10H13NO3): 230.0578.
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