4-Methylmorpholine → 2-Amino-3-chlorobenzamide

To a solution of 2-amino-3-chloro-benzoic acid (2.57 g, 15.0 mmol) in THF (100 mL) were added EDCl (3.16 g, 16.5 mmol), HOBt (2.23 g, 16.5 mmol) and N-methylmorpholine (1.67 g, 16.5 mmol). The reaction mixture was stirred at room temperature for 20 minutes then 50% (v/v) aq. NH4OH solution (4.2 mL, 60.0 mmol) was added. The mixture was stirred for 20 hours at room temperature. Solvent was evaporated and the residue was taken in ethyl acetate (200 mL). Water (100 mL) was added. The organic phase was separated; the aqueous phase was extracted with ethyl acetate (200 mL). The combined organic phase was washed with water (100 mL), then brine (100 mL), and dried over anhydrous sodium sulfate. Solvent was evaporated and dried under vacuum to give 2-amino-3-chloro-benzamide as a white solid. Yield: 2.07 g (81%).

1. stirringThe mixture was stirred for 20 hours at room temperature
2. customSolvent was evaporated
3. additionWater (100 mL) was added
4. customThe organic phase was separated
5. extractionthe aqueous phase was extracted with ethyl acetate (200 mL)
6. washThe combined organic phase was washed with water (100 mL)
7. dry with materialbrine (100 mL), and dried over anhydrous sodium sulfate
8. customSolvent was evaporated
9. customdried under vacuum

ORDレコード

ord-ccad1c881736485e8b24114df715e2df

出典データセット

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09238640B2