2-Methyl-4-nitrophenol → 4-(2-Methyl-4-nitrophenoxy)pyridin-2-amine

Temperature

150 °C

2-Amino-4-chloropyridine (5.0 g), N-methylpyrrolidone (40 ml), 2-hydroxy-5-nitrotoluene (11.9 g) and diisopropylethylamine (20.1 g) were placed in a reaction vessel, followed by stirring under a nitrogen atmosphere at 150° C. for 5 days. The reaction mixture was allowed to cool down to room temperature and concentrated under reduced pressure. To the residue was added a saturated aqueous solution of sodium hydrogencarbonate, followed by stirring overnight at room temperature. Liquid-liquid separation was carried out after addition of tetrahydrofuran (200 ml) to the reaction mixture. The aqueous layer was extracted with diethyl ether (100 ml). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The precipitated solid was suspended in diethyl ether and collected by filtration. The solid was washed with diethyl ether:ethyl acetate=1:1 and dried under aeration to provide the titled compound as a yellow solid (4.36 g, 45.7%).

1. temperatureto cool down to room temperature
2. concentrationconcentrated under reduced pressure
3. additionTo the residue was added a saturated aqueous solution of sodium hydrogencarbonate
4. stirringby stirring overnight at room temperature
5. customLiquid-liquid separation
6. additionafter addition of tetrahydrofuran (200 ml) to the reaction mixture
7. extractionThe aqueous layer was extracted with diethyl ether (100 ml)
8. washThe organic layer was washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. concentrationconcentrated under reduced pressure
11. filtrationcollected by filtration
12. washThe solid was washed with diethyl ether
13. dry with materialethyl acetate=1:1 and dried under aeration

ORD record

ord-6cb4d0cc7bed4e9788eeecef881fc425

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08288538B2