Nitric Acid → 5-Bromo-6-methyl-3-nitropyridine-2-amine

HRID 1625983Notes

Reaction equation

HRID 1625983 reaction equation
[N+:1]([O-:4])(O)=[O:2].[NH2:5][C:6]1[N:11]=[C:10]([CH3:12])[C:9]([Br:13])=[CH:8][CH:7]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:13][C:9]1[CH:8]=[C:7]([N+:1]([O-:4])=[O:2])[C:6]([NH2:5])=[N:11][C:10]=1[CH3:12]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 1706782-Pyridinamine, 5-bromo-6-methyl-

Product 1

HCID 1119015-Bromo-6-methyl-3-nitropyridine-2-amine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (2.9 ml) was added dropwise to a solution of 6-amino-3-bromo-2-methylpyridine (7.2 g) in concentrated sulfuric acid (39 ml) under ice-cooling over 30 minutes, and the mixture was stirred at the same temperature for one hour. After further stirring at room temperature for one hour, the reaction solution was poured into ice water. A 50% aqueous sodium hydroxide solution was added, and the resulting precipitate was collected by filtration, washed with distilled water and then dried under reduced pressure to give the title compound (9.0 g).

Workup

  1. temperaturecooling over 30 minutes
  2. stirringAfter further stirring at room temperature for one hour
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with distilled water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a9df8c826a79492a9ebb949defc1f04b
Source dataset
uspto-grants-2014_07
Patent number
US08785438B2

Reaction notes

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