Nitric Acid → 6-Amino-5-nitropyridine-3-sulfonic acid

HRID 2168139Notes

Reaction equation

HRID 2168139 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 4595336-Aminopyridine-3-sulfonic acid

Product 1

HCID 203244826-Amino-5-nitropyridine-3-sulfonic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
50 °C

Procedure

6-Aminopyridine-3-sulfonic acid (20 g) in concentrated H2SO4 (80 mL) was heated at 50° C. until it was completely dissolved. To this solution was added fuming HNO3 slowly over 20 minutes, so the internal temperature did not exceed 55° C. After the addition was complete, the reaction mixture was heated at 50° C. for 1 hour. After it was cooled to room temperature, it was poured into 150 g of ice. The mixture was stirred for another hour. The flask was cooled to 0° C., and was kept at 0° C. for another 2 hours. The solid was collected by filtration, and washed with cold 1:1 water/ethanol (20 mL), followed by diethyl ether (10 mL). The solid was dried in a vacuum oven overnight to provide the title compound.

Workup

  1. dissolutionwas completely dissolved
  2. additionTo this solution was added
  3. customslowly over 20 minutes
  4. customdid not exceed 55° C
  5. additionAfter the addition
  6. temperatureAfter it was cooled to room temperature
  7. temperatureThe flask was cooled to 0° C.
  8. filtrationThe solid was collected by filtration
  9. washwashed with cold 1:1 water/ethanol (20 mL)
  10. customThe solid was dried in a vacuum oven overnight

Sources & evidence

ORD record
ord-8326084892f54ccb9a179789640bd622
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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