Ammonia → 2,6-Dibromo-4-nitro-1-oxo-1lambda~5~-pyridine

HRID 712173Notes

Reaction equation

HRID 712173 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Br:8])[N+:3]=1[O-:9].[N+:10]([O-])([OH:12])=[O:11].N>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[C:4]([Br:8])[N+:3]=1[O-:9]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 944Nitric AcidHCID 5648732,6-Dibromopyridine N-Oxide

Product 1

HCID 110228822,6-Dibromo-4-nitro-1-oxo-1lambda~5~-pyridineYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
62.5 °C

Procedure

A solution of 2,6-dibromopyridine 1-oxide (34.0 g, 0.13 mol) in sulfuric acid (120 mL) was cooled to 0-5° C. followed by addition of nitric acid (60 mL). The reaction mixture was stirred at the same temperature for 10-15 min then heated to 60-65° C. for 20 h. The reaction was then cooled to rt, poured into ice-cold water and neutralized with aqueous ammonia solution. The resulting solution was stirred for 10 min at 0-5° C. then filtered and dried to obtain the desired product as a pale yellow solid (32 g, 83%).

Workup

  1. temperatureThe reaction was then cooled to rt
  2. stirringThe resulting solution was stirred for 10 min at 0-5° C.
  3. filtrationthen filtered
  4. customdried

Sources & evidence

ORD record
ord-3a636ad77e07437aaa7f94177a6ac8d2
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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