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

HRID 1845852Notes

Reaction equation

HRID 1845852 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.[N+:9]([O-])([OH:11])=[O:10]>S(=O)(=O)(O)O>[Br: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 5995293-Bromo-5-hydroxypyridine

Product 1

HCID 534184205-Bromo-2-nitropyridin-3-olYield 91.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5-Bromo-3-hydroxylpyridine (2 g, 0.011 mol) was dissolved in concentrated sulfuric acid (6 mL), fuming nitric acid (0.52 mL, 0.011 mol) was added under ice-cooling, and the mixture was stirred for 20 hours. The reaction mixture was gently poured into ice water and the mixture was stirred. The precipitated solid was filtered and washed with water to give the object product as a pale-yellow solid (2.2 g, yield 90%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. filtrationThe precipitated solid was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-3f5ea0525a974a3da1ba50a56c57728a
Source dataset
uspto-grants-2015_02
Patent number
US08951993B2

Reaction notes

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