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

HRID 1966214Notes

Reaction equation

HRID 1966214 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.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

5

Reactant 2

HCID 944Nitric AcidHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 187656985-Chloro-2-nitropyridin-3-ol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

5-Chloro-3-pyridinol (15.3 mmol) is dissolved in concentrated H2SO4 (15 ml). At 5° C. concentrated nitric acid (0.9 ml) is added. The reaction mixture is allowed to warm to room temperature over 6 days. The reaction solution is pored onto ice (50 ml) and diluted with water (200 ml). The precipitate is filtered, washed with water and dried at 40° C. in vacuo. 5-Chloro-2-nitro-pyridine-3-ol is obtained as yellow powder; mp. 97°; LC-MS (method B): 1.35 min, 175.1 (M+H+).

Workup

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

Sources & evidence

ORD record
ord-28b963c141694d5cba80518d2f5ae2cd
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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