Methyl iodide → Methyl 3-Amino-4-chlorobenzoate

3-Amino-4-chlorobenzoic acid (20.9 g, 0.122 mol) and cecium carbonate (79.5 g, 0.244 mol) were suspended in N,N-dimethylformamide (500 mL), and methyl iodide (7.60 mL, 0.122 mol) was added thereto, and then the reaction mixture was stirred under argon atmosphere at room temperature for 2 hours. Ethyl acetate (250 mL) and diethyl ether (500 mL) were added to the reaction mixture and then the whole was washed with water (1 L). The aqueous layer was extracted with ethyl acetate/diethylether (2/1) (300 mL, 3 times). The combined organic layer was washed with water (500 mL, 4 times) and saturated brine (300 mL) successively. The organic layer was dried over anhydrous magnesium sulfate and then the solvent was removed under reduced pressure to give the titled reference compound (21.82 g) as a pale brown solid. (Yield 97%)

1. washthe whole was washed with water (1 L)
2. extractionThe aqueous layer was extracted with ethyl acetate/diethylether (2/1) (300 mL, 3 times)
3. washThe combined organic layer was washed with water (500 mL, 4 times) and saturated brine (300 mL) successively
4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
5. customthe solvent was removed under reduced pressure

ORD record

ord-0653f679aebe4b1a9230f84456a855df

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420635B2