5-Aminonicotinic Acid → 5-Hydroxynicotinic acid
Reaction equation
N[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].N([O-])=[O:12].[Na+]>OS(O)(=O)=O>[OH:12][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 4.00 g (29.0 mmol) of 5-aminonicotinic acid in 400 ml of 0.1N H2SO4 at room temperature was diazotized with 2.2 g (31.8 mmol) of NaNO2 by the method of R. Graf (supra) to afford 5-hydroxynicotinic acid. The intermediate free acid was esterified in anhydrous methanolic HCl by the method of Urban (supra) to afford 2.34 g (53% overall yield) of 5-hydroxy nicotinic acid, methyl ester, mp 186°-187° C. (lit 182°-193° C.; Urban, supra). The IR data gave the characteristic 5-hydroxy band at 2550.
Sources & evidence
- ORD record
- ord-65f0e706b7f74501831c671efdf6d62b
- Source dataset
- uspto-grants-1993_06
- Patent number
- US05215738
Reaction notes
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