Nitric Acid → HCID 135671327, compound

HRID 235959Notes

Reaction equation

HRID 235959 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[CH:5][CH:4]=1.[N+:15]([O-])([OH:17])=[O:16]>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[NH:10][C:11]([N+:15]([O-:17])=[O:16])=[C:12]([CH3:14])[N:13]=2)=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 178488953HCID 178488953, compound

Product 1

HCID 135671327HCID 135671327, compoundYield 25%

Procedure

A mixture of 2-(p-methoxyphenyl)-4-methylimidazole (5.2 g, 0.0277 mole) and 3N HNO3 (125 ml) was stirred at room temperature. After 15 minutes, the mixture was placed in a preheated 90° C. bath. Heating was continued for 20 minutes and the hot solution was quenched in ice-water (250 ml). The yellow solid was collected, washed with water, and suspended in cold saturated NaHCO3 solution (25 ml). After a 15 minute period of stirring, the product was collected and recrystallized from 50% EtOH to yield 1.6 g (25%) of 41; m.p. 198°-204° C. A sample recrystallized from 50% EtOH melted at 199°-204° C.

Workup

  1. customwas placed in a preheated 90° C.
  2. temperatureHeating
  3. waitwas continued for 20 minutes
  4. customthe hot solution was quenched in ice-water (250 ml)
  5. customThe yellow solid was collected
  6. washwashed with water
  7. stirringAfter a 15 minute period of stirring
  8. customthe product was collected
  9. customrecrystallized from 50% EtOH

Sources & evidence

ORD record
ord-21f007d8e3c7429191868facc3faa74d
Source dataset
uspto-grants-1987_02
Patent number
US04642311

Reaction notes

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