4-Methylmorpholine → 2-Amino-4,6-dimethylbenzamide

To a solution of 2-amino-4,6-dimethyl-benzoic acid (0.35 g, 2.08 mmol) in anhydrous THF (10 mL) was added EDCl (0.80 g, 4.17 mmol), HOBt (0.80 g, 5.22 mmol) and N-methyl-morpholine (0.7 mL, 6.24 mmol). The reaction mixture was stirred at room temperature for 30 minutes, then ammonium hydroxide (50% v/v, 2.5 mL) was added. The mixture was stirred at room temperature for 17 hours. The solvent was removed under reduced pressure. Water (50 mL) was added, and the mixture was extracted with dichloromethane (2×100 mL). The combined organic phase was washed with water, and dried over anhydrous Na2SO4. Removal of the solvent gave the crude product. The crude product was purified by column chromatography (silica gel 230-400 mesh; 3% methanol in dichloromethane as eluent) to give 2-amino-4,6-dimethyl-benzamide. Yield: 0.20 g (59%).

1. stirringThe mixture was stirred at room temperature for 17 hours
2. customThe solvent was removed under reduced pressure
3. additionWater (50 mL) was added
4. extractionthe mixture was extracted with dichloromethane (2×100 mL)
5. washThe combined organic phase was washed with water
6. dry with materialdried over anhydrous Na2SO4
7. customRemoval of the solvent
8. customgave the crude product
9. customThe crude product was purified by column chromatography (silica gel 230-400 mesh; 3% methanol in dichloromethane as eluent)

ORD record

ord-22b6769681264ff3baf60da94c51c1e3

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2