Hydrochloric Acid → 3-{4-[(4,6-Dimethyl-3-nitro-2-pyridinyl)amino]phenyl]propanoic acid

温度

140 °C

To a solution of 2-chloro-4,6-dimethyl-3-nitropyridine (17.9 g, 96 mmol) and methyl 3-(4-aminophenyl)propanoate (19 g, 96 nmol) in DMSO (100 mL) was added N,N-diisopropylethylamine (26 g, 200 mmol), and the reaction mixture was heated at 140° C. overnight. The reaction mixture was partitioned between water (400 mL) and ethyl acetate/toluene (v/v, 2:1, 300 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate/toluene (v/v, 2:1, 200 mL). The combined organic extracts were washed with brine (200 mL), dried (Na2SO4), and concentrated. To a solution of residual oil in methanol (100 mL) was added 2 N aqueous NaOH (150 mL, 300 mmol) and the resulting mixture was stirred at room temperature for 2 h. The volatile component was removed under reduced pressure and the residue was washed with ethyl acetate (200 mL). The aqueous phase was acidified with 2N hydrochloric acid (200 mL, 400 mmol) and extracted with ethyl acetate (3×200 mL). The extracts were washed with brine (200 ML), dried (Na2SO4), and concentrated to give 23.2 g (77%) of the title compound as pale brown solids.

1. customThe reaction mixture was partitioned between water (400 mL) and ethyl acetate/toluene (v/v, 2:1, 300 mL)
2. customThe organic phase was separated
3. extractionthe aqueous phase was extracted with ethyl acetate/toluene (v/v, 2:1, 200 mL)
4. washThe combined organic extracts were washed with brine (200 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated
7. customThe volatile component was removed under reduced pressure
8. washthe residue was washed with ethyl acetate (200 mL)
9. extractionextracted with ethyl acetate (3×200 mL)
10. washThe extracts were washed with brine (200 ML)
11. dry with materialdried (Na2SO4)
12. concentrationconcentrated

ORDレコード

ord-7d0b787432fa467dbe08c4d3aa423e9e

出典データセット

uspto-grants-2006_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07141580B2