Nitric Acid → HCID 58779352, compound

HRID 1372488Notes

Reaction equation

HRID 1372488 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[N+:11]([O-])([OH:13])=[O:12].[OH-].[K+]>S(=O)(=O)(O)O>[I:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([N+:11]([O-:13])=[O:12])=[CH:9][N:10]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14797Potassium HydroxideHCID 27643276-Iodoimidazo(1,2-a)pyridine2×

Product 1

HCID 58779352HCID 58779352, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 6-iodoimidazo[1,2-α]pyridine (Intermediate 6, 448 mg, 1.84 mmol) in concentrated sulfuric acid (1.8 mL) at 15° C. was added concentrated nitric acid (0.54 mL) dropwise. After the addition was complete, the reaction mixture was stirred at room temperature for one hour and was poured onto 10 g of ice. The pH of the mixture was adjusted to 4 with aqueous potassium hydroxide solution and the resultant solids were collected by filtration, washed with water and dried. The crude product was recrystallized from dichloromethane/hexanes to afford the title compound. LC/MS 289.8 (M+1).

Workup

  1. additionAfter the addition
  2. filtrationthe resultant solids were collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe crude product was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-3321e47fa7cf44e1bc7d1959dd66e502
Source dataset
uspto-grants-2007_01
Patent number
US07157490B2

Reaction notes

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