3-Methyl-4-nitrophenol → HCID 23153294, compound

Temperature

150 °C

To a solution of 2-amino-4-chloropyridine (2.50 g, 19.4 mmol) in N-methylpyrrolidone (20 ml) were added 3-methyl-4-nitrophenol (5.94 g, 38,8 mmol) and diisopropylethylamine (13.5 ml, 77.5 mmol), followed by stirring at 150° C. under a nitrogen atmosphere. The reaction mixture was cooled down to room temperature, and diisopropylethylamine in the mixture was evaporated under a reduced pressure. The resultant residue was partitioned between ethyl acetate (150 ml) and a 1 N aqueous solution of sodium hydroxide (50 ml). The aqueous layer was extracted with ethyl acetate (50 ml). The combined organic layer was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a residue, which was then purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/2, ethyl acetate, then ethyl acetate/methanol=20/1) to provide the titled compound (1.64 g, 34.4%) as a brown solid.

1. temperatureThe reaction mixture was cooled down to room temperature
2. customdiisopropylethylamine in the mixture was evaporated under a reduced pressure
3. customThe resultant residue was partitioned between ethyl acetate (150 ml)
4. extractionThe aqueous layer was extracted with ethyl acetate (50 ml)
5. washThe combined organic layer was washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. customThe solvent was evaporated
8. customto give a residue, which
9. customwas then purified by silica gel column chromatography (eluent

ORD record

ord-b358093719b84f058f3fb3c8bbce4dd0

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531532B2