Nitric Acid → 4-Nitro-2,3,5-trimethylpyridine, 1-oxide

HRID 722104Notes

Reaction equation

HRID 722104 reaction equation
[N+:1]1([O-:10])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[CH3:9].[N+:11]([O-])([OH:13])=[O:12].C(Cl)(Cl)Cl>OS(O)(=O)=O>[CH3:9][C:2]1[C:3]([CH3:8])=[C:4]([N+:11]([O-:13])=[O:12])[C:5]([CH3:7])=[CH:6][N+:1]=1[O-:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 6212ChloroformHCID 104869072,3,5-Trimethyl-1-oxidopyridin-1-ium

Product 1

HCID 112176114-Nitro-2,3,5-trimethylpyridine, 1-oxideYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of 2,3,5-collidine-N-oxide (3.77 g, 28 mmol) in conc. H2SO4 (8 mL) was cooled to 0° C. and fuming HNO3 (5 mL, 100 mmol) was added dropwise. The resulting transparent solution was stirred at 100° C. for 24 h, cooled to r.t., poured onto ice, and the pH was adjusted to 10. Work-up (CHCl3), drying (MgSO4), and evaporation gave the title compound, (97% yield, 97% purity). Rf (MeOH/EtOAc 1:9): 0.7. HPLC Rt: 4.756 min. 1H-NMR (CDCl3): δ 8.08 (s, 1H), 2.50 (s, 3H), 2.27 (s, 3H), 2.23 (s, 3H). m/z (%) 183.1 (M+1, 100%).

Workup

  1. temperaturecooled to r.t.
  2. additionpoured onto ice
  3. customdrying
  4. custom(MgSO4), and evaporation

Sources & evidence

ORD record
ord-df5cd6ca57244bb7933ea26e002be695
Source dataset
uspto-grants-2006_11
Patent number
US07138401B2

Reaction notes

Loading…