Nitric Acid → HCID 23000195, compound

HRID 398353Notes

Reaction equation

HRID 398353 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13](=[O:14])[C:12]3=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]3[C:10]2=[O:19])=[C:4]([CH3:20])[N:3]=1.[N+:21]([O-])([OH:23])=[O:22]>OS(O)(=O)=O.O.C([O-])([O-])=O.[Na+].[Na+]>[NH2:1][C:2]1[C:7]([N+:21]([O-:23])=[O:22])=[CH:6][C:5]([CH2:8][N:9]2[C:10](=[O:19])[C:11]3=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]3[C:13]2=[O:14])=[C:4]([CH3:20])[N:3]=1

Participants

6

Reactant 2

HCID 944Nitric AcidHCID 23000271HCID 23000271, compound

Product 1

HCID 23000195HCID 23000195, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 2-amino-6-methyl-5-(phthalimidomethyl)pyridine (3.00 g, 11.2 mmol) in H2SO4 (17 mL) at 0° C. was added HNO3 (583 μL) dropwise. The solution was stirred for 1 h at 0° C. and was then warmed to room temperature at which it was stirred for an additional 3 h. The reaction was diluted with water and neutralized with solid Na2CO3. The resulting orange precipitate was filtered and washed with water. Silica gel chromatography (gradient 3% MeOH/CHCl3 to 4% MeOH/CHCl3) afforded the title compound as a bright yellow solid.

Workup

  1. temperaturewas then warmed to room temperature at which it
  2. stirringwas stirred for an additional 3 h
  3. filtrationThe resulting orange precipitate was filtered
  4. washwashed with water

Sources & evidence

ORD record
ord-c3790d849bc541df971caad0800ea138
Source dataset
uspto-grants-2003_08
Patent number
US06610692B1

Reaction notes

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