Chlorosuccinimide → methyl 4-amino-3-chloro-5-methylbenzoate

In a 300 mL three-necked, round-bottomed flask fitted with a magnetic stirrer, condenser equipped with nitrogen inlet, and thermometer were placed 5.68 (25 mmole) of methyl 4-amino-3-methylbenzoate and 35 mL of acetonitrile. The flask was immersed in a preheated oil bath (oil bath temperature 70° C.) and 5.15 g (37.8 mmole) of N-chlorosuccinimide was added all at once. The resulting mixture was refluxed for 2 hours then cooled to room temperature to stand overnight. The reaction mixture was concentrated by removing solvent using a rotary evaporator and the resulting residue was partitioned between a mixture of 100 ml of ethyl ether and 100 ml of water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was removed using a rotary evaporator, yielding 6.05 g methyl 4-amino-3-chloro-5-methylbenzoate.

1. customIn a 300 mL three-necked, round-bottomed flask fitted with a magnetic stirrer, condenser
2. customequipped with nitrogen inlet
3. customThe flask was immersed in a preheated oil bath
4. temperatureThe resulting mixture was refluxed for 2 hours
5. concentrationThe reaction mixture was concentrated
6. customby removing solvent
7. customa rotary evaporator
8. customthe resulting residue was partitioned between a mixture of 100 ml of ethyl ether and 100 ml of water
9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
10. customthe solvent was removed
11. customa rotary evaporator

ORD record

ord-7ef875f9dff048e8b92e59fc9612e16d

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05929098