Acetic Acid → 6-Chloro-2-methoxy-3-nitro-4-pyridinamine

Temperature

100 °C

2,6-Dichloro-3-nitro-pyridin-4-ylamine (733 mg, 3.52 mmol) was placed in a 48 mL pressure vessel fitted with a magnetic stir bar and treated with NaOMe (7.05 mL, 3.52 mmol, 0.5 M in MeOH). The vessel was sealed and heated to 100° C. for 2 h. The cooled mixture was treated with acetic acid (0.25 mL) in diethyl ether (50 mL). The precipitate was filtered and washed with ether, and the filtrate was concentrated in vacuo. The residue was purified on a 40-g SEPRA Si 35 SPE column (Flow rate=25 mL/min; Eluent=EtOAc-hexanes, 1:19 for 15 min, then 1:19 to 1:4 over 40 min) to yield 6-chloro-2-methoxy-3-nitro-pyridin-4-ylamine as a pale yellow solid. 1H-NMR (400 MHz, CDCl3) δ: 6.36 (s, 1H), 6.14 (br. s., 2H), 4.04 (s, 3H).

1. customfitted with a magnetic stir bar
2. customThe vessel was sealed
3. filtrationThe precipitate was filtered
4. washwashed with ether
5. concentrationthe filtrate was concentrated in vacuo
6. customThe residue was purified on a 40-g SEPRA Si 35 SPE column (Flow rate=25 mL/min

ORD record

ord-9b4bcdef27b34d6cb18dc8e2302a2394

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680098B2