Hydrochloric Acid → HCID 67119420, compound

Temperature

70 °C

An iron powder (372.9 g), 1290 ml of ethanol, 531 ml of water, and 2.8 g of a 35% hydrochloric acid were charged into a 2000-ml glass flask equipped with a stirring device, a thermometer, and a reflux condenser, and the mixture was heated to reflux. Isopropyl 4-methyl-2-nitro-5-(4-(trifluoromethoxy)phenoxy)benzoate (373 g) dissolved in 398 ml of ethanol was added dropwise thereto over a period of two hr. After reflux for 8 hr, 10 ml of a saturated aqueous sodium bicarbonate solution was added, and the mixture was filtered. The filtrate was concentrated, and 300 ml of ethyl acetate was added to the residue. The mixture was washed with brine, followed by separation. The ethyl acetate layer was concentrated under the reduced pressure. Isopropanol (320 ml) was added to the residue, and the mixture was heated at 70° C. for dissolution. Water (160 ml) was added to the solution to cool the solution. The precipitated solid was collected by filtration and was dried to give isopropyl 2-amino-4-methyl-5-(4-(trifluoromethoxy)phenoxy)benzoate (283.7 g, yield: 82.2%).

1. customequipped with a stirring device
2. temperaturea thermometer, and a reflux condenser, and the mixture was heated to reflux
3. additionwas added dropwise
4. temperatureAfter reflux for 8 hr
5. filtrationthe mixture was filtered
6. concentrationThe filtrate was concentrated
7. addition300 ml of ethyl acetate was added to the residue
8. washThe mixture was washed with brine
9. customfollowed by separation
10. concentrationThe ethyl acetate layer was concentrated under the reduced pressure
11. additionIsopropanol (320 ml) was added to the residue
12. additionWater (160 ml) was added to the solution
13. temperatureto cool the solution
14. filtrationThe precipitated solid was collected by filtration
15. customwas dried

ORD record

ord-689ead90ee1d4fedaffb808f1716e379

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367833B2