Sodium Hydroxide → 2-bromo-6-ethoxy-3-nitropyridine

HRID 2407763Notes

Reaction equation

HRID 2407763 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[K+].[Br:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH3:15])[N:8]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:6][C:7]1[C:12]([N+:1]([O-:4])=[O:2])=[CH:11][CH:10]=[C:9]([O:13][CH2:14][CH3:15])[N:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24434Potassium NitrateHCID 12010182-Bromo-6-ethoxypyridine

Product 1

HCID 8172142-bromo-6-ethoxy-3-nitropyridineYield 72%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Potassium nitrate (0.625 g) was added with stirring to a solution of the compound prepared in Example 278 (0.500 g) in sulfuric acid (2.47 mL) at 0° C. The mixture was allowed to warm up to room temperature and then heated slowly to 75° C. After heating for 2 hours, the mixture was cooled to room temperature, poured into ice, pH adjusted to 4 with 10% aqueous sodium hydroxide, and the precipitated to obtain the title compound (0.440 g) having the following physical data.

Workup

  1. temperatureheated slowly to 75° C
  2. temperatureAfter heating for 2 hours
  3. temperaturethe mixture was cooled to room temperature
  4. additionpoured into ice
  5. customthe precipitated

Sources & evidence

ORD record
ord-35655323788e4db5a3b81ad505cb993d
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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