Nitric Acid → 2-Bromo-3-methoxy-6-nitropyridine

HRID 1976044Notes

Reaction equation

HRID 1976044 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 903642-Bromo-3-methoxypyridine

Product 1

HCID 126928732-Bromo-3-methoxy-6-nitropyridineYield 65%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-3-methoxypyridine (Desc. 4; 12.4 g, 66 mmol) in concentrated sulphuric acid (30 ml) was treated dropwise with fuming nitric acid (5.5 ml), and the solution heated at 60° C. for 2 hours. After cooling the solution was poured onto ice (500 ml). The solid formed was recovered by filtration, washed with water (500 ml) and sodium bicarbonate solution (500 ml) to give the title product as a yellow solid (10.0 g, 43 mmol, 65% yield).

Workup

  1. temperatureAfter cooling the solution
  2. additionwas poured onto ice (500 ml)
  3. customThe solid formed
  4. filtrationwas recovered by filtration
  5. washwashed with water (500 ml) and sodium bicarbonate solution (500 ml)

Sources & evidence

ORD record
ord-82496e5089a54becaafaa0682c089bdf
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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