Nitric Acid → 6-Amino-5-nitropyridine-3-sulfonic acid
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
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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 dropwise over 20 minutes. The rate of addition was kept slow so that the internal temperature did not exceeded 55° C. After the addition was complete, the reaction mixture was heated at 50° C. for 1 hour. After the mixture cooled to room temperature, it was poured into 150 g of ice. The mixture was stirred for another 1 hour. The whole flask was cooled to 0° C., and was kept at 0° C. for another 2 hours. The solid was collected by filtration, and was 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 give the title compound.
Workup
- dissolutionwas completely dissolved
- additionTo this solution was added
- customdropwise over 20 minutes
- additionThe rate of addition
- customdid not exceeded 55° C
- additionAfter the addition
- temperatureAfter the mixture cooled to room temperature
- temperatureThe whole flask was cooled to 0° C.
- waitwas kept at 0° C. for another 2 hours
- filtrationThe solid was collected by filtration
- washwas washed with cold 1:1 water/ethanol (20 mL)
- customThe solid was dried in a vacuum oven overnight
Sources & evidence
- ORD record
- ord-edea7b13324e4044bd61a7dfc50c81d7
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073855B2
Reaction notes
Loading…