Nitric Acid → HCID 67213401, compound

HRID 2108386Notes

Reaction equation

HRID 2108386 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][C:11]1[CH:16]=[C:15]([N:17]2[CH:21]=[CH:20][NH:19][CH2:18]2)[CH:14]=[CH:13][N:12]=1.C([O-])(O)=O.[Na+]>>[N+:6]([CH:18]1[N:17]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([CH3:10])[CH:16]=2)[CH:21]=[CH:20][NH:19]1)([O-:9])=[O:7]

Participants

5

Reactant 4

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 67213101HCID 67213101, compound

Product 1

HCID 67213401HCID 67213401, compoundYield 66%

Conditions

Temperature
110 °C

Procedure

To a stirred solution of sulfuric acid (14 ml, 95-97%) and HNO3 (10 ml, fum.) was added at 0° C. 3-(2-methyl-4-pyridinyl)-1H-imidazole (4.0 g, 25.1 mmol). The reaction mixture was stirred at room temperature for 50 min, at 100° C. for 2.5 h and at 110° C. for 10 h and poured into ice-water (70 ml). Solid NaHCO3 was added to the stirred mixture until the pH reached 5. The solution was extracted with THF (4×200 ml), the combined organic layers were dried (MgSO4) and evaporated to give 2-nitro-3-(2-methyl-4-pyridinyl)-1H-imidazole (3.4 g, 66%) as a light yellow solid; MS (ISP) 205.2 [(M+H)+].

Workup

  1. extractionThe solution was extracted with THF (4×200 ml)
  2. dry with materialthe combined organic layers were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-46667a8fe16049b98347a38f01a48293
Source dataset
uspto-grants-2009_04
Patent number
US07514443B2

Reaction notes

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