Ammonium formate → HCID 22933920, compound

To a solution of 6-chloro-2-fluoro-3-methyl-4-nitrophenol (4.11 g, 19.9 mmol) in ethanol (200 ml) were added 10%-palladium/carbon (containing 50% water, 410 mg) and ammonium formate (15.1 g, 240 mmol), and the resulting mixture was stirred for 3 hours with heating under reflux while maintaining the temperature. The mixture was filtered by the use of Celite and the filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was partitioned by the use of water and ethyl acetate (the aqueous layer was adjusted to pH 6 to 7 with a 5% aqueous sodium hydrogencarbonate solution and re-extracted), and the organic phase was washed with a 5% aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then filtered. The filtrate was concentrated under reduced pressure to obtain 4-amino-2-fluoro-3-methylphenol (2.89 g, 100%).

1. temperaturewith heating
2. temperatureunder reflux
3. temperaturewhile maintaining the temperature
4. filtrationThe mixture was filtered by the use of Celite
5. concentrationthe filtrate was concentrated under reduced pressure
6. customto obtain a crude product
7. customThe crude product was partitioned by the use of water and ethyl acetate (the aqueous layer
8. extractionre-extracted), and the organic phase
9. washwas washed with a 5% aqueous sodium chloride solution
10. dry with materialdried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-e90945bfecde4800a7f3e03fd2b611cd

Source dataset

uspto-grants-2007_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07199147B2