2,6-Dichloro-3-nitropyridin-4-amine → 6-Chloro-2-methoxy-3-nitro-4-pyridinamine

To a stirred solution of 2,6-dichloro-3-nitro-pyridin-4-ylamine (20.0 g, 96.1 mmol) in MeOH (100 mL) was added 0.5 M NaOMe in MeOH (423 mL, 211 mmol) dropwise. The resulting mixture was stirred at room temperature for 3 h. The resulting mixture was then concentrated to ca. ⅓ of the volume and slowly poured into saturated NH4CI solution (200 mL). The resulting mixture was extracted with EtOAc (3×150 mL). The combined EtOAc extracts were dried (Na2SO4), and concentrated in vacuo to yield a tan solid which was suspended in hexane (500 mL) and sonicated for 10 min. The resulting solid was collected by suction filtration and dried under suction to yield 6-chloro-2-methoxy-3-nitro-pyridin-4-ylamine as a powder. 1H-NMR (400 MHz, CDCl3) δ: 6.39 (s, 1H), 6.28 (br s, 2H), 4.05 (s, 3H).

1. concentrationThe resulting mixture was then concentrated to ca. ⅓ of the volume
2. additionslowly poured into saturated NH4CI solution (200 mL)
3. extractionThe resulting mixture was extracted with EtOAc (3×150 mL)
4. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
5. concentrationconcentrated in vacuo
6. customto yield a tan solid which
7. customsonicated for 10 min
8. filtrationThe resulting solid was collected by suction filtration
9. customdried under suction

ORD record

ord-264a83a030414a769e97bc6437ef3323

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09409915B2