Nitric Acid → 5-Chloro-2-nitropyridin-3-ol

HRID 1966236Notes

Reaction equation

HRID 1966236 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[N+:9]([O-])([OH:11])=[O:10]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]([N+:9]([O-:11])=[O:10])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 187656985-Chloro-2-nitropyridin-3-olYield 74%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Chloro-3-pyridinol (382 mmol) is dissolved in concentrated H2SO4 (375 ml). At 5° C. concentrated nitric acid (25 ml) is added. The reaction is allowed to warm to room temperature over 3 hours. The reaction solution is pored onto ice water (5000 ml). The precipitate is filtered, washed with water and dried over night at 40° C. in vacuo. 5-Chloro-2-nitro-pyridine-3-ol is obtained as yellow powder in a yield of 74%. Mp.: 97° C.; LC-MS (Method B): 1.35 min, 175.1 (MH+).

Workup

  1. filtrationThe precipitate is filtered
  2. washwashed with water
  3. customdried over night at 40° C. in vacuo

Sources & evidence

ORD record
ord-dbe0202107b443f19a0a90458ce0329b
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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