Nitric Acid → 2,6-Dibromo-3-methoxy-5-nitropyridine

HRID 2391744Notes

Reaction equation

HRID 2391744 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[C:8]([Br:14])[N:7]=1>S(=O)(=O)(O)O>[Br:5][C:6]1[C:11]([O:12][CH3:13])=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([Br:14])[N:7]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 113346372,6-Dibromo-3-methoxypyridine

Product 1

HCID 127582082,6-Dibromo-3-methoxy-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To 150 ml of concentrated sulfuric acid were added at 0° C. 150 ml fuming nitric acid. 40.0 g of 2,6-dibromo-3-methoxypyridine (example E2) were added portionwise to this mixture at 0° C. The reaction mixture was stirred for 45 minutes at 0° C. and then heated to 65° C. for 2 h. The mixture was poured into 2 l of crushed ice and stored at 0° C. overnight. The resulting precipitate was filtered, washed with water and dried under vacuum to yield the title compound.

Workup

  1. temperatureheated to 65° C. for 2 h
  2. waitstored at 0° C. overnight
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-29832a3e2df74f73985855f5b8eb8b9b
Source dataset
uspto-grants-2012_09
Patent number
US08273890B2

Reaction notes

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