2-Methoxyaniline → 2-amino-6-chloro-N-(2-methoxyphenyl)benzamide

SO2Cl2 (5.4 mL, 74 mmol, 2.5 eq) was added to a rapidly stirring solution of 2-amino-6-chlorobenzoic acid (5 g, 29.14 mmol) in benzene (146 mL) and the mixture was stirred at reflux for 24 h. The mixture was concentrated under reduced pressure, and stripped down twice with benzene to give brown oil. The resulting oil was dissolved in CHCl3 (146 mL) and to that solution was added o-anisidine and the mixture was stirred at 65° C. for 2 h. The mixture was cooled to rt and the resulting precipitate was removed by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography on a 120 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane over 20 min as eluent to provide 2-amino-6-chloro-N-(2-methoxyphenyl)benzamide as yellow solid. 1H NMR (DMSO-d6) δ ppm 9.44 (1 H, s), 7.86 (1 H, dd, J=7.9, 1.3 Hz), 7.13-7.21 (1 H, m), 7.04-7.11 (2 H, m), 6.97 (1 H, t, J=7.6 Hz), 6.66 (2 H, dd, J=28.0, 7.9 Hz), 5.37 (2 H, s), 3.81 (3 H, s). Mass Spectrum (ESI) m/e=277.0 (M+1).

1. temperatureat reflux for 24 h
2. concentrationThe mixture was concentrated under reduced pressure
3. customto give brown oil
4. stirringthe mixture was stirred at 65° C. for 2 h
5. customthe resulting precipitate was removed by filtration
6. concentrationThe filtrate was concentrated under reduced pressure
7. custompurified by column chromatography on a 120 g of Redi-Sep™ column
8. customover 20 min

ORD record

ord-068d06b487524e01a422647a0cc53acc

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07919498B2