2-chloro-3-nitro-6-hydroxypyridine Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

Appearance

Light brown to brown Solid

Safety Information

HS Code 

2933399990

2-chloro-3-nitro-6-hydroxypyridine Usage And Synthesis

Synthesis

2-Chloro-6-methoxy-3-nitropyridine (20.85 g, 110.57 mmol) was used as starting material and suspended in concentrated hydrochloric acid (37%, 171 mL, 5528.49 mmol). The reaction mixture was stirred at 90 °C for 3 h and subsequently cooled to room temperature. The pH of the reaction mixture was adjusted to 5 with 2 M NaOH solution, and then the aqueous phase mixture was successively extracted with ethyl acetate (EtOAc, 250 mL). The organic phases were combined and concentrated to give a yellow solid. The solid was filtered and washed with ether (Et2O, 200 mL). The solid was re-suspended in ethyl acetate (200 mL), stirred and filtered to remove the insoluble green solid. The filtrates from the two filtrations were combined, dried with anhydrous magnesium sulfate (MgSO4) and concentrated to give 6-chloro-5-nitropyridin-2-ol as a yellow solid (14.7 g, 84.22 mmol, 76% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 6.52 (1H, d), 8.26 (1H, d), no OH peak was observed. Mass spectral analysis showed m/z 173 (MH)+.

References

[1] Patent: WO2009/24821, 2009, A2. Location in patent: Page/Page column 142-143
[2] Patent: US2016/75711, 2016, A1. Location in patent: Paragraph 0792-0793

2-chloro-3-nitro-6-hydroxypyridine(198268-98-3)Related Product Information

• 2-Chloro-3-nitropyridine-6-amine
• 6-Chloro-5-nitropyridine-2-carboxylic acid