Methyl 4-(2-chloroethoxy)-5-methoxy-2-nitrobenzoate → Methyl 2-amino-4-(2-chloroethoxy)-5-methoxybenzoate

Temperature

50 °C

In a 50 mL volume glass flask equipped with a stirrer, a thermometer, a reflux condenser and a gas inlet were placed 1.02 g (3.45 mmol) of methyl 5-methoxy-4-(2-chloroethoxy)-2-nitrobenzoate (purity: 98%) obtained in Reference Example III-2 and 20 mL of methanol. The resulting mixture was heated to 50° C. under stirring. To the mixture was added 0.5 g of 3 wt. % platinum sulfide/carbon (containing 65.7% water) at the same temperature. The resulting mixture was heated to the same temperature for one hour, while hydrogen was introduced to the mixture under atmospheric pressure at a rate of 50 mL/min. After the reaction was complete, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure, to precipitate a crystalline product. The crystalline product was dried under reduced pressure, to give 0.91 g (isolated yield: 93.0%, purity: 99% in terms of area percentage determined by high performance liquid chromatography) of methyl 5-methoxy-4-(2-chloroethoxy)-anthranilate as a white crystalline product.

1. customIn a 50 mL volume glass flask equipped with a stirrer
2. additionwas introduced to the mixture under atmospheric pressure at a rate of 50 mL/min
3. filtrationthe reaction mixture was filtered
4. concentrationthe filtrate was concentrated under reduced pressure
5. customto precipitate a crystalline product
6. customThe crystalline product was dried under reduced pressure

ORD record

ord-e3ae948c013b4cef846c166c4518d8e0

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367824B2