4-Methylmorpholine → 2-Amino-6-chlorobenzamide

To a solution of 2-amino-6-chlorobenzoic acid (2.00 g, 11.65 mmol) in anhydrous THF (20 mL) were added 4-methylmorpholine (1.40 mL, 12.82 mmol), HOBT (1.73 g, 12.82 mmol), and EDCl (2.45 g, 12.82 mmol); the reaction mixture was stirred at room temperature for 30 minutes. 50% (v/v) Ammonium hydroxide solution (10 mL, 132.0 mmol) was added and the mixture was stirred at room temperature for 23 hours. Solvent was evaporated to about 20 mL, poured into aqueous NaHCO3 solution (200 mL) and extracted with ethyl acetate (7×100 mL). The organic phase was washed with water (3×100 mL), dried (Na2SO4), filtered, and evaporated, to give 2-amino-6-chlorobenzamide as a white solid. Yield: 1.65 g (83%).

1. stirringthe mixture was stirred at room temperature for 23 hours
2. customSolvent was evaporated to about 20 mL
3. additionpoured into aqueous NaHCO3 solution (200 mL)
4. extractionextracted with ethyl acetate (7×100 mL)
5. washThe organic phase was washed with water (3×100 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. customevaporated

ORD record

ord-e999ea58282e448b8b5f86b06a4c0cf9

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2