Nitric Acid → 5-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamine

HRID 727222Notes

Reaction equation

HRID 727222 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1.[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[NH2:1][C:2]1[C:7]([N+:11]([O-:13])=[O:12])=[C:6]([CH3:8])[C:5]([Br:9])=[C:4]([CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 110308555-Bromo-4,6-dimethylpyridin-2-amine

Product 1

HCID 36499475-Bromo-4,6-dimethyl-3-nitro-2-pyridinylamine

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4 g (20 mmol) of the product obtained in Stage A are dissolved in 16 ml of concentrated sulfuric acid with stirring and cooling in ice. The solution is brought to 55° C. and 1.3 ml of concentrated nitric acid are added dropwise, care being taken to maintain the temperature between 55° and 60° C. The stirring is continued for 20 minutes and the mixture is then poured onto crushed ice. The product is precipitated by addition of 40% sodium hydroxide. It is filtered off, washed with water and then dried. 3.7 g of product are thus collected. The product is recrystallized from 95° C. ethanol.

Workup

  1. temperaturecooling in ice
  2. customis brought to 55° C.
  3. temperatureto maintain the temperature between 55° and 60° C
  4. additionthe mixture is then poured
  5. customonto crushed ice
  6. customThe product is precipitated by addition of 40% sodium hydroxide
  7. filtrationIt is filtered off
  8. washwashed with water
  9. customdried
  10. custom3.7 g of product are thus collected
  11. customThe product is recrystallized from 95° C. ethanol

Sources & evidence

ORD record
ord-c6268f0f22a04bdc8c602ddee7371ca8
Source dataset
uspto-grants-1998_01
Patent number
US05712294

Reaction notes

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