Nitric Acid → 6-Methyl-2-nitropyridin-3-ol

HRID 367085Notes

Reaction equation

HRID 367085 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.[N+:9]([O-])([OH:11])=[O:10]>OS(O)(=O)=O>[OH:1][C:2]1[C:7]([N+:9]([O-:11])=[O:10])=[N:6][C:5]([CH3:8])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 142752-Methyl-5-hydroxypyridine

Product 1

HCID 848016-Methyl-2-nitropyridin-3-olYield 36.3%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

5-Hydroxy-2-methylpyridine (23.6 g, 216 mmole)was dissolved in conc. H2SO4 (50 mL) and cooled to 0° C. Fuming HNO3 (50 mL) was added over one hour. The solution was stirred at room temperature for one hour, poured onto ice (400 g), and filtered. The solids were dissolved in EtOAc washed with brine (100 mL). The organic extracts were dried (MgSO4), and the solvent was evaporated to yield 12.1 g (36.3%) of the title compound. mp 102-105° C. 1H NMR (DMSO-d6, 300 MHz) δ: 2.44 (s, 3H), 7.52 (d, J=8.5 Hz, 1H), 7.58 (d J=8.5 Hz, 1H). MS (ESI -Q1MS) m/e 153(M-H)+. Anal. calcd. for C6H6N2O3C, 46.76 H, 3.92; N, 18.18 Found: C, 46.65 H, 3.98; N, 18.10.

Workup

  1. additionpoured onto ice (400 g)
  2. filtrationfiltered
  3. dissolutionThe solids were dissolved in EtOAc
  4. washwashed with brine (100 mL)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-1578c4faa2494d9196d35c6b34b581e1
Source dataset
uspto-grants-2000_10
Patent number
US06133253

Reaction notes

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