Nitric Acid → 2-Amino-5-bromo-4-methyl-3-nitropyridine

HRID 2088949Notes

Reaction equation

HRID 2088949 reaction equation
[N+:1]([O-:4])(O)=[O:2].[Br:5][C:6]1[C:7]([CH3:13])=[CH:8][C:9]([NH2:12])=[N:10][CH:11]=1.[OH-].[Na+]>S(=O)(=O)(O)O>[Br:5][C:6]1[C:7]([CH3:13])=[C:8]([N+:1]([O-:4])=[O:2])[C:9]([NH2:12])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 8176952-Amino-5-bromo-4-methylpyridine

Product 1

HCID 72132072-Amino-5-bromo-4-methyl-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

Nitric acid (0.7 ml) was added dropwise to a solution of 5-bromo-4-methylpyridine-2-amine (2.0 g) in concentrated sulfuric acid (8.7 ml) at 55° C. over 30 minutes, and the mixture was stirred at the same temperature for 3 hours. After further stirring at room temperature for 2 hours, 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 (2.5 g).

Workup

  1. stirringAfter further stirring at room temperature for 2 hours
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with distilled water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-d7027121a6224fed84dc13fd104b1e31
Source dataset
uspto-grants-2013_05
Patent number
US08436012B2

Reaction notes

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