Nitric Acid → 8-(4-Nitrophenyl)imidazo[1,2-a]pyridine

HRID 1982539Notes

Reaction equation

HRID 1982539 reaction equation
[C:1]1([C:7]2[C:8]3[N:9]([CH:13]=[CH:14][N:15]=3)[CH:10]=[CH:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[N+:21]([O-])([OH:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>O>[N+:21]([C:4]1[CH:3]=[CH:2][C:1]([C:7]2[C:8]3[N:9]([CH:13]=[CH:14][N:15]=3)[CH:10]=[CH:11][CH:12]=2)=[CH:6][CH:5]=1)([O-:23])=[O:22]

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 137640278-Phenylimidazo[1,2-a]pyridine

Product 1

HCID 233169598-(4-Nitrophenyl)imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

Add 20 g (0.10 mole) of the product from Example 4 slowly to 150 ml of concentrated sulfuric acid at -15° C. Add 7 ml of concentrated nitric acid slowly, maintaining the temperature -10° C. Stir at -10° C. for 30 minutes. Pour onto 500 g of ice. Add 2 L of water and neutralize with potassium carbonate. Extract with three 500 ml portions of methylene chloride. Combine the extracts, dry over magnesium sulfate, treat with charcoal and remove the solvent in vacuo. The residue is crystallized from ether to provide the title compound.

Workup

  1. extractionExtract with three 500 ml portions of methylene chloride
  2. dry with materialdry over magnesium sulfate
  3. additiontreat with charcoal
  4. customremove the solvent in vacuo
  5. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-0ebf47bbc4ac40cca43b8ef2d7408410
Source dataset
uspto-grants-1986_06
Patent number
US04596872

Reaction notes

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